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English Pages 74 [39] Year 2023-2024
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Anus
Chemistry 216 Course Pack Synthesis and Gumball Watteison
Characterization of Organic
Compounds
Department of Chemistry
John P. Wolfe, Ph.D.
University of Michigan
Ginger Shultz, Ph.D.
2023-2024
macmillan learning curriculum solutions
Table of Contents
Course Pack Instructions Course Learning Goals Calculations Guide .. .. . ..
Copyright
2023 by John P. Wolfe and Ginger Shultz
Photos provided by Hayden-McNeil, LLC
5-6 7-9
Recrystallization Guide
11-12
Thin Layer Chromatography Guide ................. Separations Guide
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17-19
Spectroscopy Quick Reference Guides
21
Infrared Spectroscopy Table
23-24
NMR Spectroscopy Table
25
Practice Problems for Quizzes All rights reserved.
13-16
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Course Pack Instructions CHEM 216 builds on the experimental approach started in CHEM 211. In this course you will
use microscale equipment, which will require you to develop manual dexterity and You will evaluate the results of your experiments by
care in working in the laboratory.
checking for product identity and purity using various analytical methods, including IR and NMR spectroscopy, TLC, and melting point. You will be expected to keep laboratory notebook, and to complete worksheets where you analyze results or answer other questions related to the experiment. For some experiments you will work in small groups, and for
each
group project, your group will formulate hypotheses that you will test using
experiments that you design and implement with faculty and GSI guidance.
02 1
The front pages of this course pack are intended to provide you with resources that will
help you prepare for, conduct, and analyze the results of your experiments. These include
a description of the learning goals for the course, guidelines for maintaining : lab notebook, crafting a hypothesis, and carrying out calculations you will need to conduct experiments. There are also guides provided on some of the common experimental techniques such as TLC and recrystallization.
Although the majority of this course is focused on laboratory experiments, you will be
introduced to some reactions you have not (and will not) encounter in the Chem 210 and Chem 215 lecture courses. In addition, you will also learn to analyze and interpret IR and
NMR spectra. The majority of the
pages in this course pack consist of problems, taken
directly from quizzes given in past semesters, that spectroscopy problems and other course related topics.
will
help you practice solving
The answer key for this coursepack is not contained within these pages, but instead posted as file on Canvas. We advise you use the answer key appropriately, and with
caution
make to create
the presence of an
too easy for
one
answer key can be an
impediment to learning; answer keys
to confuse the ability to understand an answer with the ability
answer/solve a problem. Be aware that some problems may have more than
one possible answer that is consistent with data presented. Our recommendation that you do not save all problems for the few days prior to the quiz, but rather work on the
problems as the topics come up throughout the course of the semester.
Course Learning Goals The primary goal of the course is to build on concepts of structure and reactivity from
Chemistry 210 and 215, as
you
learn to predict the behavior of compounds that they
use in lab. The experiments in Chemistry 216 are problem-based and are designed to engage you with authentic but accessible problems, which practicing organic chemists routinely encounter in lab. This is based on a learning model that says that meaningful learning occurs when we make mistakes doing difficult tasks rather than
when we are repeatedly successful :
easy ones. The learning objectives are aimed at
building competency in laboratory technique and developing scientific process skills, while simultaneously reinforcing concepts around structure and reactivity. The specific learning goals
of the course are described below. Use them to assess your
progress through out the
term.
LABORATORY TECHNIQUES Lear1
Goals
1. Thin Layer Chromatography a. Understand the purpose and applications of TLC b. Explain how TLC (or chromatography) works Select ppropriate solvents & adjust solvent ratio to optimize resolution and position of spots
d. Interpret TLC to differentiate between starting materials, products, and e.
impurities Use TLC to monitor a reaction or column
f. Use TLC in combination with other information to identify an unknown 2.
compound Recrystallization
a. Understand the purpose of recrystallization
b. Explain how recrystallization works d. e.
3.
Select appropriate solvents for single and mixed solvent recrystallization Successfully purify reaction products using recrystallization Recover crude product from mother liquid if recrystallization fails
Calculations d.
b. C.
Understand what crude yield, % yield, and theoretical yield are, how they
differ, and what information is gleaned from each Calculate crude yield, % yield, theoretical yield
Explain concentration, how it differs from "amount", and why it is important
to know d.
Explain what a molar equivalent is and how it is used Convert between moles, molarity, density, and molar equivalents
SPECTROSCOPY Learning Goals a. Explain what spectroscopy is, differentiate between IR and NMR, the type b.
of information provided by each, and their limitations Use: spectral database to obtain
IR, NMR, and m.p. data
Calculations Guide For each experiment you will need to do some calculations in your lab notebook before
you get to and
1.
Infrared Spectroscopy
Identify the main components of an Infrared spectrum (units, regions, peak
characteristics)
Identify major functional groups and bonds in the functional group region
using a table
c. Interpret authentic spectra collected in lab and identify if it corresponds to product, starting material,
lab. To
get started you should read over the procedure (posted on CTools)
identify quantities of reagents that aren't useful to you in their present form. For
instance, in the example procedure shown below you are asked to dissolve 0.01 mol of N-allylaniline in dichloromethane to give a molar solution. You can't measure
moles or molarity
that you know how
directly so you'll need to convert to either grams or milliliters so ch of each reagent to measure out. See the example calculations
below as model for how to determine the quantity to measure in lab starting from
moles, molar equivalents or molarity.
or reaction/recrystallization solvent
d. Compare spectra obtained in lab to spectral data from the literature e. Match a set of compounds the appropriate IR spectrum f.
Use an IR spectrum along with other characterization methods to identify unknown compounds Use
an
IR spectrum, with and without other information, to predict a
molecular structure 2.
NMR Spectroscopy a.
Interpret features of a spectrum including: 1) number of peaks; 2) peak position; 3) integration; and 4) splitting, to determine fragments or the
complete structure of a compound b. Do reverse interpretation starting from
structure predict number of
CH2Cl2 1.0 equiv
1.2 equiv
N-alllylaniline
allylisocyanate
N..-Diallyl-N1-Phenylurea
MW = 133.19
MW = 83.09
MW = 216.13
Example Procedure (brief): Dissolve 0.01 mol of N-allylaniline in dicholoromethane to give a 1 molar solution. Add 1.2 molar equivalents of allylisocyanate and stir at rt for 1 h. Evaporate solvent and recrystallize product.
peaks, peak position, integration and splitting in a spectrum. C.
Interpret coupling constants and use them to differentiate between
d.
Interpret both 'H and 13C NMR and be able to differentiate between the type
This procedure afforded 1.6 g of the product.
structural isomers
e.
f.
of information that can be obtained by each Match a set of compounds to the appropriate NMR spectrum Use an NMR spectrum, with and without other information, to predict a
Converting Moles to Grams:
molecular structure
determine, such as mass or volume. To convert moles to grams we multiply fractions using the molecular weight of the component of interest. Molecular weights are typically given in amu (atomic mass units), but these values are
Use an authentic NMR spectrum, along with IR, m.p., and TLC, to identify an unknown compound
Compare an authentic NMR spectrum obtained in lab to spectral data from
We
cannot (easily) directly measure moles. So,
that we can easily
we need to convert that unit to one
the same as grams/mol. So,
the literature
1 mole of N-allylaniline = 133.19 g To calculate grams of a reactant starting from moles we do the following:
Moles of reactant x molecular weight of reactant (grams / mol) = grams of reactant Applied to our example procedure,
we need to determine
starting from moles (0.01 mol). We do the following:
grams of N-allylaniline
0.01 mol x 133.19g/1mol = 1.3319 g (which can
weigh with some accuracy.
we can round up to
1.33 g - a value we
We can
calculate the amount of allylisocyanate needed (0.012 mol) manner; 0.012 mol x 83.09g/1mol = 0.9971 g (which we can round up to can weigh with some accuracy).
After each experiment you will need to calculate the yield of product that you obtained
help us relate the moles
of one
reagent to the moles of another.
the moles of N-allylaniline. To do this we multiply the moles of one reagent times the molar equivalents of the other;
Moles of first reagent x molar equivalents of second reagent = moles of second reagent Applied to our example procedure, we need 1.2 molar equivalents of allylisocyanate N-allylaniline). Because we start with 0.01
mol
of N-allylaniline we
determine the amount of allylisocyanate by multiplying 0.01 X 1.2 0.01 mol x 1.2 = 0.012 mol So,
Calculating Percent Yield
1.00 - a value we
on
to
M solution we
same as
in a similar
From our example procedure we need to calculate the moles of allylisocyanate based
(relative
dissolve 0.01 mol of N-allylaniline in dichloromethane to give a
need to dissolve 1.33g of N-allylaniline in 0.01 liter of dichloromethane (which is the
Molar Equivalents: Molar equivalents
So
e cd
as a
measure of how efficient the reaction was. Typically this is given as a
percent
yield. Before you calculate percent yield you need to know the theoretical yield.
Theoretical yield is the maximum amount of product that can possibly be formed in a reaction. This is equal to the amount (in moles) of the limiting starting reagent (the one present in the lowest molar amount. So in this case, the theoretical yield of the urea product is 0.1 mol (the same as the N-allylaniline, which is the limiting reagent). To calculate theoretical yield we need to convert moles to grams again: 0.01 mol x 216.13 g/mol = 2.1613 g (which we will round to 2.16). Out theoretical yield in this case is 2.16g of product. Once you have theoretical yield you
can
use that along with the actual yield to
determine the percent yield. For percent yield of the reaction we divide amount
obtained by theoretical amount possible and multiply by 100. So, if we obtain 1.6 g of product:
we need to use 0.012 mol of allylisocyanate.
% yield = (1.6g/2.16g) x 100 = 74%
Molarity to give mL of solvent in a solution:
Calculating Percent Yield of an Unknown Compound
To calculate the mL of dichloromethane needed to prepare a allylaniline in dichloromethane you need to do the following:
molar solution of N-
The
So, a 1 molar (M) solution of N-allylaniline would contain
To dissolve
mole of N-allylaniline per
need to convert grams to moles.
0.01 mol of N-allylaniline in dichloromethane to give
M solution we
use the following information. M
mole/liter; and 0.01 mol of N-allylaniline = 1.33 g (we calculated this above)
We then solve the following equation: 0.01 mol/X liters
1
mol/1 liter
unknown starting material to prepare
an
is to first try to assign the structure of the product and then use the molecular weight
molarity of a solution is defined as moles of material dissolved in 1 liter of solvent.
liter of solvent. To calculate how to form a solution
For some experiments you will use an
unknown compound and will be asked to identify (assign a structure to) this unknown product. The best way to calculate percent yield for your unknown product
Calculating Molarity (when preparing solutions):
The answer is 0.01 liter
of that structure to calculate the percent yield as above.
Recrystallization Guide Recrystallization is a technique that is used to purify compounds. The first identify a suitable recrystallization solvent
step is
to
by determining the solubility of your
compound in the solvents that are available in the lab. This can be done empirically, but you can save yourself some time and effort by predicting which solvents your compound will or will not be soluble in. Start with the general rule of thumb "like
dissolves like" Generally speaking, polar solvents (i.e. water) dissolve polar or ionic
compounds, and nonpolar solvents dissolve nonpolar compounds. There are a few details that you should keep in mind. Halogenated solvents (i.e. dichloromethane) are relatively nonpolar as compared to oxygen containing solvents like diethyl ether.
Solubility also depends on how many hydrocarbon groups (-CH2-) are present in the
compound you are trying to dissolve. Compounds with less than 4 carbon atoms and an O or N atom tend to be water soluble.
water soluble
NOT water soluble
Once you've used your chemical knowledge to select a few solvents to try, you can the solubility of your compound. To test the solubility of compounds that are liquid at room temperature add about 0.1 ml of the liquid to about mL of solvent. If it dissolves it is soluble. For compounds that are solid at room temperature you can add 40 mg of the compound to 1 mL of solvent and then stir the mixture for minute or two to see if the
naterial dissolves Keep in mind that solubility is a relative term, and
that a compound can be partially soluble in a solvent. In fact, partial solubility is what are looking for, as solvents in which your compound is partially soluble are ideal for recrystallization. Case C: compound i not soluble at low dissolves with increasing temperature
high
Case A: compound is soluble in this solvent at all temperatures
solubility
Casel
low
compound is not soluble
any
solubility high
temperature
emperature
Temperature has an influence on solubility. Therefore when identifying a solvent for recrystallization you should test the solubility of your compound in the solvent of interest as heat is applied. The ideal solvent for recrystallization is one that will
dissolve your compound only when the temperature is increased (see Case C above). When no single solvent is ideal for recrystallization of a compound, a mixed solvent 11
10
recrystallization can be performed using a combination of one solvent in which your
compound is soluble at room temperature (Case A) and one in which your compound is not soluble at any temperature (Case B),
Procedure
add drops
of
solvent to the solid until the material is just barely dissolved. It's important
the warm
to use the minimum amount of solvent possible; the most common reason for failed
recrystallizations is using
too much solvent. After dissolving the compound, gravity filter the solution to remove any
insoluble impurities, and rinse the filter with a small the desired product.
Finally,
allow the liquid to cool slowly to room temperature. The more slowly it cools the more molecules have to order themselves into
crystal arrangement. If after
~10 minutes no crystals appear you can place the container in an ice bath to facilitate
crystallization.
To recrystallize a compound using a combination of two solvents (i.e. solvent A and B
above) you will need to warm small amount of each solvent. In this
case we'll use
ethanol and water as an example, because it is a common combination for mixed solvent recrystallization. Many organic compounds are soluble in ethanol, which can as our solvent "A" and many organic compounds
will serve as our solvent "B",
are insoluble in water, which
is used to separate
identity of an unknown compound.
of reactions, and 3) aid in determining the
How it works
TLC uses a stationary phase and a mobile phase. The stationary phase is made up
of an adsorbent, like silica, that is fixed to I surface. The mobile phase or eluent
is an organic solvent that passes over the stationary phase, carrying compounds
GSI will demonstrate how to develop and analyze a TLC
plate
in your lab section.
Predicting the order of elution We can make rough predictions about how far different compounds will travel Although size and shape also influence the
in ethanol
influence the distance traveled by using more
warm ethanol r "A"
or
you reach the saturation point of the compound. First add dissolved. Then slowly add drops of water
mixture turns slightly cloudy. Finally add a few additional drops of ethanol This ensures
that you have reached a ratio of warm ethanol:water that will dissolved the compound, but have used the smallest volume of solvent possible to achieve done this you can continue in the same manner
as
described above for single solvent recrystallization.
12
less polar compound
more
drops of ethanol to the solid until it is just
dissolution. Once you have
will have a
less polar solvents. For
example, if you want a more polar compound to travel further on the plate,
the first step is to alternate between adding warm ethanol and warm
until the cloudiness dissipates (the small particles of solid re-dissolve).
on the plate or the "order of elution."
distance traveled, we typically use polarity to predict the elution order.
The adsorbent is typically silica gel, which is quite polar. This quality means that very polar compounds
provided in later section.
until the
mixture i
compound i
spotted onto
placing it in a container with a small amount of solvent (eluent or mobile phase). While it develops, the solvent will travel up the plate and carry compounds with it. Individual compounds have different affinities for the adsorbent and eluent based on their polarity, size, and shape, which causes them to travel
more polar solvent (i.e., ethyl acetate) rather than less polar solvent (i.e., hexanes) as the eluent. Guidance for selecting solvents is
In this case
TLC plate, with silica adsobent layer acting as 'stationary phase
with it.
To prepare for TLC, a small amount of a compound or mixture is first spotted onto the stationary phase on a TLC plate. Then, the plate is developed by
you might select
water to your solid until
compounds based on
greater affinity for the adsorbent and spend more time on the stationary phase when the plate is being developed. Less polar compounds will have a lesser affinity for the stationary phase and travel farther on the plate. We can
crude product
warm H-O or "B"
of chromatography,
different distances on the plate and to be separated. TLC was introduced in Chemistry 211, and your Chemistry
Procedure for a mixed-solvent recrystallization
serve
(TLC) Guide
like all forms
to 1) evaluate the purity of :t product compound, monitor the progress
for single-solvent recrystallization
amount of additional warm solvent to minimize loss of
Thin layer chromatography TLC,
differences in properties like polarity, shape, and size. In Chemistry 216, you will use TLC as a diagnostie technique
To recrystallize a compound using a single solvent, slowly
chance the
Thin Layer Chromatography
13
polar compound
Calculating
Rf
FL.C is a qualitative technique. We can evaluate the purity or identity of a compound based on how far the compound travels on the plate relative to other compounds. To make more precise comparison, we can quantify the distance traveled by measuring the distance (with a ruler) and distance the compound traveled and om and the eluent traveled
calculating an Rf value. The Rf value is the ratio between the
Co-spotting technique
Co-spotting i It is the
For example, if a compound inthertkossinset.tnstihew.09ethecrRrensded.omtc.hamghndheromnupnaendgyravndesdl distance the
eluent (solvent) traveled.
TLC technique that we use to directly compare two compounds (or samples) on the
most basic and
the plate:
frequently used technique you should use routinely. We spot compounds 1) compound A, 2) compounds A & B together, and 3) compound B.
same
TLC plate.
on three "lanes" on
traveled
Spot the plate
When spottng
as
usual
Compounds A & B
the
are different
otting one compound,
2 cm
Rf of A = 2/3 = 0.67
wait for itto completely dry, then
1.5 cm
Rf of B = 1.5/3 = 0.5
reference for your i
Compounds A & B are the same ( similar
spot the second compound.
The center lane (A&B) sei
helptull your compounds
vo similar Rf values.
Rf value should always I
reported as a decimall
Selecting a solvent as the eluent for TLC A critical part of using TLC
selecting a solvent
as your
eluent (mobile phase). First, your compound
mixture
must be soluble in the solvent you select, and the solvent must be available in the lab. Second, your compound should be
sufficiently polar so as to attract the compound, carry it up the plate, and separate it from other compounds.
Sometimesmuke multiple solvents are used. The best solvent (or solvent mixture) is one that will give you good resolution. informed predictions about which
We
solvent or combination of solvents will work
ultimately have to evaluate the solvent empirically (try it out") to ensure it works.
best. Still.
Methanol
ill. Rxn 3
? material
isolated from
acetanilide
reaction
Ethanol Acetonitrile
mixture
standard
A
Acetone
another
"Dichloromethane
Chloroform
Diethyl Ether
Least Polar Toluene
"Hexanes'
In the examples above, plate i (reaction 1) shows that spots
*Good TLC solvents that are available in the 216 lab
hexanes. Dichloromethane is often
acetate, dichloromethane, diethyl ether, and good solvent to try first because oderately polar and dissolves most
ethyl acetate and hexanes are the most commonly used solvent system and work well in relative portions of ethyl acetate (relatively polar) and hexanes (relatively nonpolar) to achieve the desired separation of our compounds Often a suggested solvent or solvent mixture will be combination because you can adjust the
Ethyl Acetate
2:1
(polar)
Hexanes Ethyl Acetate
poorly resolved
better
14
Rf values. Because the
not yield the desired product. Plate ifi (reaction 3) shows spots with comparable Rf values in the middle of the plate,
reaction yielded the desired product. We also see a second spot at lower Rf in lane A, which indicates that an impurity present. Finally, on plate iv (also reaction 3), the reaction mixture is compared to the product standard and the starting material so that can more conclusively determine the identity of the impurity in lane
the
Because it has a similar Rf value to the lower spot in lane C (starting material), we can infer that the mixture
contains both
the desired product and unreacted starting material.
provided in your lab procedure. Sometimes you will need to select one or optimize the ratio of your mixture. Work systematically and adjust the solvent ratio until your TLC plate is well resolved. Hexanes (non polar) resolved
A and B have the same or similar
Rf values of the isolated material and the standard are similar, we can infer that the reaction likely yielded the desired With plate ii (reaction 2), we see that the Rf values are quite different, and can infer that the reaction did
product.
suggesting that
Common TLC solvents available in Chemistry 216 include ethyl compounds. Mixtures of
starting material aniline
(desired product)
*Ethyl Acetate*
middle of the plate anc are distinct from
TLC plates from four reactions are shown below.
we
Most Polar Hg0 (not a good solvent for TLC) Good resolution: the spots appear somewhere in the
Compare a reaction product to a commercially available standard We can use TLC to evaluate whether a reaction has produced the desired product and whether the product is pure.
1:1 Hexanes to Ethyl Acetate good resolution
15
Monitoring the progress of reaction Pinaily, we will use TLC to monitor the progress of the on
which you
Separations Guide
reaction. To do this, you can prepare:
series i f TLC plates
co-spot a standard of the desired product of the reaction (©), the reaction mixture (B), or the starting
material (A) and develop the plate. You then repeat this intervals in the reaction. For example, at the start of the reaction, you might expect to see that the reaction mixture has a spot with an Rf value that is comparable to the starting material standard (plate i). As the reaction progresses, may that starting material spot is still the present but that a new spot appears that corresponds to the product standard (plate ii). Finally, when the starting material spot disappears, the reaction is complete (plate iii).
Extraction and washing are two primary separation techniques used by organic chemists to separate product compounds from solvents, impurities, and side products after reaction is completed. Extraction and washing are
essentially
the same technique with different goals. The goal of extraction is to extract your desired product compound from your reaction mixture containing impurities. The goal of washing is to wash impurities from the
mixture, leaving purified product behind. Using a separatory funnel
Chemists typically use a special piece of glassware called a separatory funnel to
. 1 min elapsed
ii. 30 min
elapsed
ili. 1 hour elapsed
reaction mixture
cyclohexanone
standard
A B
Density table: Solvent Water (H2O) Diethyl ether
ABC
(desired product)
Comparing an unknown compound to standard compound to determine it's identity We can use ILCI
gather evidence that helps us determine the identity,
an unknown compound. You need to have
access to a standard sample (lane B) of the compound you think you have so
that 1
1 compare it t
the unknown
sample (lane A). If the Rf values of both spots are similar, that along with other data (i.e., NMR or IR spectra), can be used to determine the identity of your unknown.
stopper
2
Density g/cm 0.999
0.713 1.327 Dichloromethane Tetrahydrofuran (THF) 0.888
Hexanes
0.661
Ethyl acetate
0.902
top layer, lower density liquid
bottom layer,
higher density liquid
A crucial note: Never dispose of a layer until you are
you'll never need
it again. You can easily mistake which layer your product is in, and once you put it in the waste, you can get it back!
?
To set
unknown compound
Two
have a greater affinity for based on these characteristics. This will help you decide which layer to keep. Chemists build an intuition about this with practice, and your GSI can help you think this through.
B
cyclohexanol
conduct an extraction or wash.
immiscible liquids are introduced into the funnel and will form two layers (figure 1). The liquid with the lowest density will float on the top. This means you can use density to determine which layer is which (see the density table for common organic solvents below). The characteristics of your product compound and the impurities, for example, their overall polarity, whether they are charged or neutral, and their capacity to form hydrogen bonds, can be used to predict which liquid layer a given compound will end up in. You have to decide which solvent the compounds vill
acetanilide standard
up the separatory funnel, begin by attaching a ring clamp
the bars
in the back of your hood or to a ring stand. Next, place your funnel in the ring and put a clean container (beaker or vial) under the funnel. You will need
at least two clean containers ready to collect each layer. Keep one container under the
beaker
funnel at all times to ensure you don't lose anything if something
goes wrong. Ensure the stopcock is always horizontal (closed) except when venting the funnel (more on this below). When ready, carefully add your two
liquids and your reaction mixture as indicated in your experimental procedure. One liquid is typically water, and the other is pure organic solvent that is immiscible in water. One layer
should float on top of the other.
Once your liquids are added you need mix them allow the impurities and product to migrate to the layer they most affinity. That means they will either stay in the reaction mixture liquid or migrate to the pure solvent. To mix them, place the stopper at the top of the funnel. Prepare to lift the funnel out of the ring stand. Place one hand
have the
top of the stopper to secure it and place the other hand on the lower part of the funnel in a way that allows support it and manipulate the stopcock as needed. Carefully lift the funnel and invert it so that the stem is pointed at an upward angle. The funnel stem should be pointed into your fume hood. Gently swirl the liquids while venting. As you swirl, solvent vapor can build up. So, it is necessary periodically by carefully turning the on the
you to
stopcock intermittently while swirling. You may hear the gaseous solvent leaving from the stem, particularly
17
mere volatile solvents like diethyl ether. Repeat the gentle swirling with venting stopcock is in the closed position and replace the funnel on the ring stand.
two more times.
Make sure the
Apply what you have learned 1)
Evaluate the solvent pairs below and decide which solvent would form the top layer in your separatory funnel. Circle the solvent that will
Remove one liquid layer
from the funnel by slowly turning the
stopcock to open and toggling to close to control the flow rate.
Carefully watch the line between the layers o ensure that you stop before you get to the second layer. Add additional pure solvent and
repeat the
extraction two more times by again swirling and venting layer of solvent. Once you have extracted (or washed) your product 3 times, you combine the layers and remove the
with the
solvent as directed.
be
on top.
a.
Diethyl ether
b.
Dichloromethane
and
C.
Tetrahydrofuran
and
and
water
2) Evaluate the Lewis structures of the solvents, product compound, and impurities shown below and draw a
line between
the molecules and the solvent layer you expect it to migrate to during mixing. Keep mind characteristics including overall polarity, whether they are charged or neutral, and their capacity to form
hydrogen bonds, can be used to predict which liquid layer they
classmate.
CH3CH2OH diethyl ethor
Na
OCH2CH,
separatory at both the top and bottom. making
sure to support the stopper
wert the funnel
r hood to
prepare for venting.
18
19
will end up in. Discuss your
infrared Spectrosco y Tabie Functional Group Na Alv
cm1)
Shape and Intensity
C-H 2960 – 2850
ht SeVed p
H .
H t
C-H 3080-3020
„H
HgC
Sharp, meaI n uI On
C=C 1620-1680
Sharp *
C-H 3100-3000
Sharp, strong
C=C 1600-1580
Sharp, strong
1-Prop n
-CEC-CH Propyn
Aromatic Rings H
H
1C e
c
H. H*
*C
c"
Ber
-
c
0 -H
H
-
0-H
Men
ylic Acids
Formic acid
Wpt0II
.
0-H 3000-2500
Rro
C=0 1725-1700
Sharp, very strong
C=0 1725-1705
Sharp, very surong
C=0 1685-1665
Sharp, very strong
Acetone
HgC "CHg
1.ro-CH
H C
3-Penten-2-one
Nuclear Magnetic Resonance Spectroscopy Table Functional Group Names & Example Compounds
Absorption Ranges (cm-) (single absorption unless noted)
Aldehydes
C=0 1730-1720
C-H 2900-2800 Ethanal
Shape and Intensity
Sharp, very strong Sharp, variable
& 2750-2700 (2 peaks)
Type of Hydrogen Atom
Type of Hydrogen Atom
RCH3
0.9
RCH2R
1.3
cyclic R3CH
7.3
1.5
1.5-2.0 1.8
Esters
CH3 Methyl formate
H.C
C=0 1750-1740
Sharp, very strong
C-O 1300-1000
Sharp, medium
R'
RCH 2.0-2.3
RNH2
RCCH3
3-5
2.3
Ethers
C-O 1300-1000
Sharp, medium
Diethyl ether
RCNHR
CH3
Amines (primary)
N-H 3500-3300
Sharp, medium
(two peaks)
CECH
2.5
RNHCH2
2-3
RCH2X (X= CI, Br,
3.5
ROH
1-5
3.8
Ethylamine
Amines (secondary)
ROCH&,RCOCH3 N-H 3500-3100
Sharp, medium
(one peak)
R2C=CH2
5.0
RCH=CR2
5.3
10-13
RCOH
CH3
H.C
H
13C NMR
N-Methylethylamine
Nitriles
Type of Carbon / RCH2CH3 C=N 2300-2200
Sharp, variable
RCH2CH3
R3CH
H-C-CEN
125-150
25-38
~20
Sharp, strong
& 1385-1345
RCOCH3 RCH2CI
Nitromethane
RCH2Br N-H 3500-3350
Sharp, medium
C=0 1680-1650
Sharp, very strong
RCH2NH2 RCH2OH RC=CH
RC=CH Methanamide
125-140 117-125
RCCH3 N=0 1560-1515
Amides
RCEN
16-25
~30
Methanenitrile
Nitro Groups
Type of Carbon Atom
RCH=CH2 13-16
RCH=CH2
170-175
RCOR
40-45
177-185
28-35
RCOH
37-45
190-200
50-64
RCH
67-70
74-85
205-220
RCR
115-120
25
II. (20 points)
1 (20 points)
A The tollowing reaction was recently reported (J. Am, Chem. Soc. 2015, 137, 11246). Using the information provided following questions.
below, please answer the
OSO-CFs
A. In the synthesis of acetanilide, 0.03 moles of aniline were treated with 1.2 molar equivalents of acetic anhydride this information, please answer the questions below:
Given
Pd(OAc)2 (4 mol %)
t-BuPHOX (10 mol %) CH2Cl2
toluene, 95 °C
Molecule: MW
316.29 g/mol
Pyrrolidine Lithium tert-butoxide MW 71.12 g/mol 80.08 g/mol density = 0.852 g/mL
Aniline
Product 2
93.13 g/mol
= 237.35 g/mol
Acetic Anhydride 102.99 g/mol molar equivalents
MW
molar equivalent 0.03 moles
This reaction was conducted using: 320 mg of Molecule 0.099 mL of pyrrolidine 1.4 molar equivalents of Lithium tert-butoxide
(a) Calculate the mass (in
Acetanilide 135.16 g/mol
(b) Calculate the
of
theoretical yield (in
acetic anhydride that was added to
of acetanilide in this
the reaction mixture. Please round to
The reaction formed 231 mg of Product
reaction.
two decimal places - X.XX g.
Please round to two decimal places - X.XX g
(a)
Calculate the amount, in moles
of molecule
that was used in this
(c) This reaction afforded 2.67 g
reaction.
of acetanilide product. Calculate the percent yield of this reaction.
5
Please round to four decimal places X.XXXX moles.
(b) Calculate the amount, in moles, f pyrrolidine that was used in this reaction. B
Please round to four decimal places - X.XXXX moles.
The acetanilide you hi
ynthesized is to be examined for new, undiscovered, biological activity. For this
experiment to be conducted, you mi to afford a 0.1 Molar solution.
take 0.1 g of acetanilide and dissolve it in dimethyl sulfoxide (DMSO)
(c) Calculate the mass, in grams, of lithium tert-butoxide
Calculate the amount of dimethy! sulfoxide solvent
that was used in this reaction.
(in mL) required to prepare a 0.1 M solution of acetanilide starting with 0.1g of acetanilide. Please
Please round to three decimal places . X.XXX g.
d) Calculate the
round to two decimal places - X.XX mL.
yield
of Product :
Please round to
two significant figures - XX%
28
29
11. (14 points)
II. (20 points)
A. In the synthesis of acetanilide, 4 mL of aniline
information, please answer the questions below:
treated with 1.2 molar equivalents of acetic anhydride. Given this
A. In the
synthesis of ethyl benzoate, 1 g of benzoic information, please answer the question below:
is
dissolved in ethanol at a concentration of 0.2 M. Given this
H2SO4
HO Aniline
MW = 93.13 g/mol d = 1.022 g/mL
Acetic Anhydride
MW = 102.99 g/mol
Acetanilide 135.16 g/mol
= 1.08 g/mL
(a) Calculate the volume (in mL) of
(b)
5
B Rank the
MW = 150.18 g/mol
reaction.
This reaction afforded 2.8 g
acetanilide product. Calculate the percent yield of this reaciton.
Ethyl Benzoate
MW 46.07 g/mol I= 0.789 g/mL
122.12 g/mol
(a) Calculate the volume of ethanol (in mL) used in the
acetic anhydride that was added to the reaction mixture.
Ethanol
Benzoic Acid MW
catalytic
CH3
(b) If the reaction provides ethyl benzoate in an 80% yield, how
5
much ethyl benzoate i produced by the reaction (in g)?
following compounds in order of increasing carbonyl stretching frequency B. Rank
A
C
the following compounds in order of increasing carbonyl stretching frequency
NH2
write the correct letter in e: A
B
write the correctletter in each box
highest wavenumber stretch
lowest wavenumber stretch
highest wavenumber stretch
30
lowest wavenumber stretch
31
6
Water
MW = 18.0 g/mol d = 1.00 g/mL
III. (15 points)
IV. (20 points) A. For the structure and IR spectrum shown below,
carresponding streches in IR spectrum.
match the labeled carbonyl groups on the molecule
with the
Number Letter
A. Your friend is
process of
pharmacist, who has made a serious mistake, and needs your help to fix it. During
stocking small bottles from larger ones, samples of Cardizem (a calcium channel blocker used to treat hypertension and angina) and caffeine were placed into unlabeled bottles, and then accidentally mixed up. Fortunately, you can figure which substance is in which bottle using IR spectroscopy. Given the IR data below (one spectrum is caffeine and the other is Cardizem), write the letter corresponding to a specific carbonyl group in either caffeine or Cardizem next to the
frequency of the IR stretch that corresponds to the carbonyl in the box below.
Hint: if two or more carbonyls appear to be structurally similar, be sure to think carefully about resonance when
making your assignments.
IR Spectrum 2
IR Spectrum 1 A: 1766 cm-1
B: 1723 cm71
1699 cm-t
1743 cmt
1659 cm-
1679 cm-t
1671
(H3C)2N Cardizem
r corresponding with stretching frequency
Caffeine
Hint: 1715 cm7i 1727 cm7
B
B. An experimental procedure indicates that an organic product should be extracted from water into dicholoromethane (CH2C12). Given the density of water (1.0 g/mL) and dichloromethane (1.33 g/mL), indicate which layer in the separtory funnel is water, and which is dichloromethane.
A student conducting the reduction of ketone A to alcohols B and C monitored the reaction by TLC. A drawing of a
TLC plate is shown below. In lane 1 of the TLC plate the student spotted an authentic sample of pure ketone A. In lanes 2-4 the student spotted a sample from the reaction mixure at time intervals of 15 min, 30 min, and 1 h from the start of the reaction. Given the data below
answer the following questions.
The top layer is
3 cm
circle one): Water CH2Cl2
The bottom layer is (circle one): Water
CH2Cl2
21
NaBH4
CH;CH2OH C.
(minor)
(major)
Based on the TLC data shown below, answer the following questions.
lane 1 = A lane 2 = rxn mix @ 15 min
Lane
lane 3 = rxn mix @ 30 min
(a) How much time is needed for the reduction of A to proceed to completion (i.e., no starting material remains)? 15 min
< 15 min
60 min
30 min
.6 cm
(b
min
boxes provided below.
B
and C are (circle one answer)
different conformations
the same molecule
constitutional isomers B
Hi value
enantiomers Hi value
diastereomers
returned only starting material; no product was formed
The starting material was completely consumed, but no product
(c) What is the relationship between products B and
and major product B and enter the values in the
Based on this TLC, which of the following statements is true (circle one).
The reaction
circle one answer
(b) Calculate the Rf ralues for starting material A
= starting material
Lane 2 = sample from reaction mixture Lane 3 = authentic sample of desired product
lane 4 = rxn Mix @ 60 min
(a) What is the Re of the desired product (TLC lane 3)?
The product was formed, no side products
material remains. • The
was
formed
are present, but some unreacted starting
starting material was completely consumed, desired product was formed,
and side products were also formed.
The starting material was completely consumed,
formed
33
and only desired product was
B. Based on the TLO data shown below, answer the following questions.
B. The reduction of benzophenone with NaBH , was carried out, and the resulting alcohol product was purified by
column chromatography Four fractions were collected from the column, and these were analyzed on the TLC plate
Passible Unknown Lane
shown below.
= aniline
Lane 2 = unknown aniline derivative 2.8 cm
NaBH,
CH;CH2OH
(a) Which spot on the TLC plate corresponds to he ketone starting material (circle one)?
(a) What is the Rip of the
(b) What
unknown aniline (TLC lane
aniline (write the compound number i
structure in the chart above corresponds to the unknown
B
A
below)?
(b) Which fractions contain (circle all that apply)?
the alcohol
3 cm
2 cm
The esterfication of p-chlorobenzaldhyde with ethanol wascarriedout,and by column chromatography Four fractions were collected from the column
shown below
(c) Calculate the Rf values for both spots (A and B)
resulting ester product was purified these 1 analyzed 1 the TLC plate
and
enter the value in the boxes provided below B
HgSO4 CHaCH2OH
OCH-CH3 + H.O
Af value
(a) Which spot on the TLC plate corresponds to the carboxylic acid starting material (circle one)?
4 cm
B
The reduction of propiophenone was carried out Upon completion the reaction
aqueous mixture
was extracted with ethyl acetate.
quenched with water and the
A
CH,CH:OH
(b) Which fractions contain the ester product (circie apply)?
During the extraction procedu
B
Rf value
(c) Calculate the Af values for both spots (A and B) and enter the value in the boxes provided below.
organic
(ethyl acetate) layer
which layer will be on the bottom (circle one)? ethyl acetate and water will not separate into two layers
aqueous
(water) layer
B
Ht value
Rf value
After the organic layer is removed from the aqueous layer
this remove from the organic layer (provide a structure
35
3
stirred with magnesium sulfate What word answer)?
does
1S)
CI I WIve In Speclra DelOw Wion thne corresponding compounds in tne fadle. Inaicale your diSWel Dy piacng
0 CH O (solvent)
IR. 1740 cm "oCH
a ||
to s o ).1II
HC. Hjć
IVI
* CH
tI▇ ▇
▇uI- - ▇ talI 1 ▇
▇ IV,V-uII I U al
IU ▇
▇
II W,Il
SaI y""
I(12ponis
p
DuNVIVne1I a M N VV1LILII
1 tT
Compound
tt▇
▇ LC
▇
1T ▇ ▇
1▇ ▇
▇▇
Match the four NMR spectra below with the corresponding compounas in Ue laDie. Iucate your cnowcr ) piow
Sompound
, o
CH
e
Mtch the NMR spectra DeOW WI tFe cUr p unmg 11
p uT u▇ tTe teI ▇ T GTate y ▇ anTouvGt ▇
Spectrum Number
*po
ich the four NMH spec
Cnetri nn nunnla
3H, S
. i,
.O 3H, t
C T
d. 1H t, T t, 1H|d, 1H
,
t d, 1
H, s
3H, s
3H, s
d. 1
d,
r in t
nn
ri ta
1. (15 points) Match the
I. (15 points)
five NMA spectra below with the corresponding compounds in the table. Indicate your answer by placing
the spectrum number in the appropriate space. Spectrum number
Spectrum 1:
Match the five NMR spectra below with the corresponding compounds in the table. the spectrum number in the appropriate space. Spectrum
Compound Structure
number
Indicate your answer by placing
Spectrum 1
Compound Structure
m, 2
m. 2
Spectrum
Spectrum 3
Spectrum
Spectrum 4:
Spectrum
m, 2
m,
t, 3
Spectrum 5
m, 1 m, 1 m.
44
*
*|
Match tne five NMR spectra Delow Wiln tne corresponang copounas In tne table, Inalcate your answer by plad
poln
Match the fivenumber C NMR inspectra below withspace. the corresponding compounds in the table. Indicate your answer by piacing the spectrum the appropriate Spectrum
Con
)=
h
00-
16o14o
0 14o
Spectrüm .a
Spectrum 5
I. (15 points)
1. (15 points)
Match the five C NMR spectra below with the corresponding compounds in the table Indicate your answer by placing the spectrum number in the appropriate space. Spectrum 1:
Spectrum number
Compound Structure
Match the five C NMR spectra below with the corresponding compounds in the table. the spectrum number in the appropriate space. Spectrum number
Compound Structure
Spectrum 2:
Spectrum 3:
Spectrum 2:
Spectrum 4:
200 180 160 14
Spectrum 3:
Snectrum
Spectrum 5:
Snartrum
48
Spectrum 1:
Indicate your
by placing
1. (15 points)
II. (x points)
Match the five C NMA spectra below with the corresponding compounds the spectrum number in the appropriate
space.
table. Indicate
your answer by placing A. For each of the compounds below predict
Spectrum 1:
Spectrum Compound Structure number
the number of peaks (ignore coupling) in the 1H and 13C NMR
spectra.
Proton NMR: Number of Peaks
Ratio of Peaks
Carbon NMR: Number of Peaks
H3C,
Proton NMR: Number of Peaks
Ratio of Peaks
Spectrum 2:
Carbon NMR:
Number of Peaks
Proton NMR: Number of Peaks
Ratio of Peaks
Carbon NMR: Number of Peaks
Spectrum 3:
Spectrum 4:
B. NMR spectroscopy is a useful tool for analyzing mixtures of compounds, as integration can be used to determine the ratio of products present in
mixtures. A proton NMR spectrum was obtained for the mixture of A, B,
and D shown
below. This spectrum showed four single peaks, one for each of the components. The peaks were integrated, and the observed ratios are also provided below. Given this information, answer the following questions: CH3
H3C-Si-CHs
HaC-CEN
HaC CH3
CHa C
B
Chemical Shift:
Integration ratio:
2.10
3
2.62
12
Spectrum 5:
a. Which compound is present in the largest amount
(the highest molar concentration). Circle the letter that corresponds to your answer.
b. Which compound is present in the smallest amount (the lowest molar concentration). Circle the letter that corresponds to your answer.
A
D
3 50
51
Page 2 A. For each of the compounds below predict the number of peaks in the 1H
I1. (15 points)
and 13C NMR spectra. A.
'H NMR:
For each of the compounds below predict the number of peaks (ignore coupling) in the H and 13C
13C NMR:
Proton NMR: Number of Peaks
13C NMR: CH
1H NMR:
Ratio of Peaks
Carbon NMR: Number of Peaks
3 Proton NMR: Number of Peaks
1H NMR:
13C NMR:
13C NMR:
Ratio of Peaks
Carbon NMR: Number of Peaks
Proton NMR: Number of Peaks
B. NMR spectroscopy is a useful tool for analyzing mixtures of compounds, as integration
determine the ratio
NMR spectra
'H NMR:
products present in mixtures. A proton NMR spectrun
A, B, C, and D shown below. The peaks corresponding to each compound
can be used to was obtained for the mixture of
Ratio of Peaks
Carbon NMR: Number of Peaks
vere integrated, and the observed questions.
ratios are also provided below. Given this information, answer the following
3. NMR spectroscopy is a useful tool for analyzing mixtures of compounds, as integration can be used to determine
the ratio of products present in mixtures.
Chemical Shift:
A
B
3.2
3.53
A proton NMR spectrum was obtained for the mixture of A, B, C, and D
shown below. This spectrum showed four single peaks, one for each of the components. The peaks were integrated, and the observed ratios are also provided below.
1.11, 3.56, 5.19
Given this information, answer the following questions:
4.8 H.C
Integration ratio:
CH2Cl2
HaC-CEN
9:6:3
10
Chemical Shift:
2.17
5.10
2.10
Integration ratio:
9
a. Which compound is present in the largest amount (the highest molar concentration). Circle the letter that corresponds to your answer.
ABCD
b. Which compound is present in the smallest amount (the lowest molar concentration). Circle the letter
corresponds to your answer.
c
a. Which compound is present in the largest amount (the highest molar concentration). Circle the letter that corresponds to your answer. that
D
3
D b.
Which compound is present in the smallest amount
(the lowest molar concentration). Circle the letter that corresponds to your
52
B
11. (21 points)
I. (20 points)
A. For each of the compounds below predict the number
CH3
of peaks (ignore coupling) in the 1H and 3C NMR spectra.
Proton NMR: Number of Peaks
A. For each of the compounds below predict the number of peaks
Ratio of Peaks
(ignore coupling) in the 'H and 13C NMR spectra
Proton NMR: Number of Peaks
Carbon NMR: Number of Peaks
Carbon NMR: Number of Peaks
Proton NMR: Number of Peaks
Ratio of Peaks
Proton NMR: Number of Peaks
Carbon NMR: Number of Peaks
Carbon NMR: Number of Peaks
OCH3
Proton NMR: Number of Peaks
Proton NMR: Number of Peaks
Ratio of Peaks
Carbon NMR: Number of Peaks
Carbon NMR: Number of Peaks
5 B. For
the structure and NMR spectrum shown below, match the labeled hydrogen atoms on the molecule with the
corresponding signals in the proton NMR spectrum.
B. For the structure and NMR spectrum shown below, match the labeled hydrogen atoms corresponding signals in the proton NMR spectrum.
Number Lettel
molecule with the
E
B s,3
Number Letter
CH3
D
F
s, 3
S, 3
B
t, 2
d,2 d,2
C
6
broad,
54
55
I1. (21 points)
II.
A. For each of the compounds below predict the number of peaks (ignore coupling) in the
Proton NMR: Number of Peaks
H and 13C NMR spectra.
(20 points)
A. For each of the compounds below predict the number of peaks (ignore coupling) in the 1H and 13C NMR spectra
Ratio of Peaks
Proton NMR: Number of Peaks
Ratio of Peaks
CHa
Carbon NMR: Number of Peaks
CH3
OH
Proton NMR: Number of Peaks
Ratio of Peaks
CH3
CH3 CH3 CH3
Carbon NMR: Number of Peaks
Proton NMR: Number of Peaks
Ratio of Peaks
Carbon NMR: Number
I Peaks
Proton NMR: Number of Peaks
Ratio of Peaks
Carbon NMR: Number of Peaks
Proton NMR: Number of Peaks
Ratio of Peaks
CHg
Carbon NMR: Number of Peaks
CHa
: For the structure and NMR spectrum shown below, match the labeled hydrogen atoms on the molecule with the
corresponding signals in the proton NMR spectrum.
Carbon NMR: Number of Peaks
B. For the structure and NMA spectrum shown below, match the labeled hydrogen atoms on the molecule with the
corresponding signals in the proton NMR spectrum.
B
Number
C Letter
Letter
CH3
D B
D
m,1
C
E
HSP-41-39
pom 56
m, 2
E m, 2
2 c II. Name
A. For each of the compounds below, predict the number of peaks in the 'H and 13C NMR spectra. B. For the bolded hydrogens in each molecule, indicate whether these equivalent (will both appear as one signal), or not equivalent (will appear as different signals).
I1. (18 points) A. For
each of the compounds below predict the number of peaks (ignore coupling) in the 1H and 13C NMR spectra
Circle the correct answer.
Proton NMR: Number of Peaks
Carbon NMR: Number of Peaks
OCHa
OCH3
'H NMR: Number of Peaks
13C
NMR: Number of Peaks
equivalent not equivalent
Proton NMR: Number of Peaks
1H NMR: Number of Peaks OH
Carbon NMR: Number of Peaks
13C NMR: Number of Peaks
equivalent not equivalent
B. For the structure and NMR spectrum shown below, match the labeled hydrogen atoms on the molecule with the corresponding signals in the proton NMR spectrum. NOTE: The H-atom attached to oxygen is not visible due Ic broadening.
HaCO
1H NMR: Number of Peaks
D
13C NMR: Number of Peaks
5
equivalent
not equivalent
Number
S,
H3C
C. For the structure and NMR spectrum shown below, match the labeled hydrogen atoms on the molecule with the corresponding signals in the proton NMR spectrum.
Number
Letter
d, 3
A
10 B
m,
m, 1
D
m, 2 2 pts each
58
C B
t, 2
E
the bolded n alogens In eacn mO18cule, Inalcale Wn urer tnese are equivalent (WIII DO n appea
jgnals). Circle the correct answer. (1 poi
IV. (20 points)
Provide the structure of a molecule with the chemical formula CsHe
below
H
NVM
CH,
ČH,
|
IR: 3061, 2947
CH3
m
WValent
the NMR signals (letters) to the numbered protons in the structure belo
13C NMR
33 2 3 4 5
6 8 2 t, 4 T y uIIIS or
C Hg0?
S, 2, br
" e
ta and the I R
IV. (20 pon
( UpoII
Provide the structure of a molecule with the chemical lormula CjH 20, that is consistent with the NMR spec
Provide hel0W. the structure of a molecule with the chemical formula CyH40, that is consistent with the NMR spectra shiown 1 NMH
1
IR: 3020, 2913, 17 16 Cm
1739 Cm
d, 2 d, 2
13C NMR
eaks (numbered below)
98
yL A
CyH 20,?
functional group
hase0 OI U 1
NMR data and the IR
for mo1e u
CH03
What functional goup 1
1
U
I
I I(
IV. (20 points)
Provide
B For
the structure of a molecule with
the chemical formula C13H 16O2 that is consistent
with the NMR spectra shown
below.
not
the bolded hydrogens in each molecule, indicate whether these are equivalent (will both appear equivalent (will appear as two different signals) Circle rect answer (1 point each)
as
one signal),
d, 6
IR: 3085 (br), 2953, 2869, 1708 cm-1
Note: There is also a broad signal at
d, 3
12 ppm with an integration of 1 H
equivalent
equivalent
equivalent
d,2
9.1
not
equivalent
not equivalent
not
equivalent
13C NMR 10 peaks (numbered below)
B. Based on the proton NMR spectrum and IR
1 shown below (for the product), draw the complete Lewis structure of
the product formed in the following reaction (no generic "R" groups - draw
6+7
I structure).
PPh,
CH>Cl2
8
Product structure
H NMR and IR data for Product IR: 1722 cm-1
200
180
100
60
COG-13-:
d, 2
How many units
of unsaturation for molecule
S.3
C13H18O2?
What functional group(s) are present based on the
NMR data and the IR stretches labeled above?
structure
64
for CyyH1gOg that fits the data above 10 65
* |IU po
(0p
Provide the structure of a molecule with the chemical formula C H 00, that is consistent with the NMR spectra sho
Provide the structure of a molecule with the chemical formula C H0, that is consistent wih
belo
1 NM
IR: 1770 cm-1 atl
1 C NMR
so
U
IV. (10 points)
IV. (20 points)
Provide the structure of a molecule with the chemical formula CgH120 that is consistent with the NMR spectra and the IR data shown below.
Provide the
structure of a molecule with the chemical formula C5H10O that is consistent with the NMR spectra
shown
below.
m, 2
'H NMR
m, 2
IR: 3328 cm-1
m, 2
m, 2
n, 2
'H NMR
IR: 2960, 2719, 1728 cm-1
S,
HSP-43-200
d, 2
ppr
13C NMR 1 peaks (numbered below)
13C NMR 6 peaks
200
200
160
140
120
100
80
60
How many units
of unsaturation for molecule
C5H10O?
What functional group(s) present based on NMR data and the IR stretches labeled above?
structure for C6H120 that fits the data
68
10
structure for C5H1oO that fits the 69
data above
10
po
Provide the structure of a molecule with the chemical formula C NO that is consiSlent Witn the NMR Spectra and tne l a 0 aa
Page S u
enoctra shoW bel0W. H NMR
IR 1 , m & Z
,
, 17 14 CI1
a
*.ii e
C NMR
IR: 2958, 2872 cm C NMR -
WV
ANv
(19
IV. Name:
3 C
points)
Provide the structure of a molecule with the chemical formula C-H-NO that is consistent with the NMR spectra and IR data shown below.
IlI. Name:
Provide the structure of : molecule with the chemical formula spectra and IR data shown below.
CoH,BrO that is consistent with the NMR
IR: 3375, 2925, 1650, 1606 cm IR:
2925, 2855, 1698 cm-1
t, 3H
a, 2H
s, 1H . 1H
1H.
.1H
11C NMR 8 peaks labeled below
13C NMR 9 peaks labeled below
2 36
220
180
140
200 180
120
How many units
How many units
of unsaturation
of unsaturation for molecule
for molecule
140
120
100
80
60
40
C,H,BrO?
C.HgNO?
Indicate (name or draw)
Indicate (name or draw) one
160
8
one functional group present in the molecule based on the NMR data and the IR strectches
functional group
present in the molecule based on the NMR data and the IR streciches
structure for CyHgNO that fits the data above 10
labeled above?
72
labeled above?
structure for CgH-BrO that fits
73
the data above 15
IV. (19 points) Provide the structure of a molecule with the chemical formula G8H1402 that is consistent with the NMR spectra shown below
TH NMR
d, 61
IR: 1725, 1661 cm-1
d,2
0,3 d, 1
13C NMR
peaks (numbered below)
180
160
100
30
CDS-01-069
(a) How many units of unsaturation
(d) Draw the structure of the molecule
molecule CgH14O2? (b) What functional group is present
a macmillan learning
based on the IR stretch at 1725 cm
and the C NMR signal at 167 ppm? (C)
curriculum solutions
What functional group is present based the IF stretch at 1661 cm
and the
NMR signals at 123 and 144 ppm?
10 g1
3
structure for CgH1402 that fits the data above
10