135A_Practice_EXAM_4(Karty3e)_KEY(1)
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CHEM 135-A
Practice Test for Exam 4 (Karty3e)
KEY
1.
(10 pt) How many signals would you expect in the
1
H NMR and in the
13
C NMR spectra
of the following compounds.
# signals in H NMR
# signals in
13
C NMR
2.
(30 pt)
Draw the principal organic product(s) expected from the following reactions.
3.
(5 pts) Arrange the compounds below in order of INCREASING reactivity toward toward
nucleophilic acyl addition.
____
B
______
<
_____
D
____
<
_____
C
____
<
_____
A
_____
Least Reactive
Most Reactive
4.
(5 pts) Arrange the compounds below in order of INCREASING chemical shift in the H
NMR spectrum.
____
D
_____
<
____
A
_____
<
____
C
_____
<
____
B
______
Smallest
Largest
5.
(40 pts) Circle ONE answer for each of the following ten multiple choice questions.
a.
Which of the following reagents will transform hexanenitrile to 1-hexanamine?
(A) NaBH
4
(B) LiAlH
4
(C)
LDA
(D) NaBH
3
CN
b.
What set of alkyl halide (1) and carbonyl compound (2) will provide 2-methyl-2-pentene
when submitted to the reaction conditions shown?
(A)1-bromobutane and acetone
(B) 1-bromopropane and acetone
(C) 2-bromopropane and butanal
(D) 2-bromopropane and ethanol
c.
What products are produced when the cyclic compound shown is hydrolyzed in aqueous
acid?
d.
CIRCLE the letter that corresponds to the carbon atom that appears the furthest
DOWNFIELD in the C13-NMR spectrum?
e.
What starting material will
NOT
result in formation of the alcohol shown when it’s
reacted with phenylmagnesium bromide followed by an acid work-up?
(A)Butanoic acid
(B) Butanoyl chloride
(C) Methyl butanoate
(D)Butanoic anhydride
f.
What products are obtained from the following sequence of reactions.
g.
What is the major product of this reaction?
h.
What is the product formed in the following reaction?
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Related Questions
Bb.84.
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a. Identify A,B,C, and D in the following equations?
OH
OH
A
CH₂-CH₂
OH OH
LOH
H3O
C
D
Br
B
b. How many signals would you expect in the 1H NMR spectrum of HOCH2CH2CH2CH2OH?\
c. The ¹H NMR spectrum of bromoethane shows a signal at 3.5 ppm when the spectrum is recorded using a 60 MHz spectrometer. Where do you expect to see the signal if a 300
MHz instrument is used instead?
d. SHow the splitting pattern of the protons in the following compound?
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10
NMR: 69.8 (1 H, s), 8 1.1 (9 H, s)
Deduce the structure of the unknown compound.
Select
/|||||||
G
C
Draw
Rings
More
Erase
Q2 Q
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QUESTION 9
Propose a structure for a carboxylic acid with molecular formula C6H10O2 by interpreting the following 13C NMR spectra.
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For the compound given below, sketch the proton decoupled ¹3C NMR spectrum
and DEPT 135 and 90 spectra.
H3C.
1
2
3
(ethoxymethoxy)ethane
4
CH3
5
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Please help annotate all of the spectra in the picture below, thank you so so much! It is C NMR, H NMR, and MS!
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What protons in alcohol A give rise to each signal in its 1H NMR spectrum? Explain all splitting patterns observed for absorptions between 0 to 7 ppm.
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Please elaborate thoroughly one by one how the answer was obtained and double check if the answers are correct, wrong or lack. Thank you!
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Which one of the following compounds (from Figure #7) produced the
'H NMR spectrum (from Figure #8) shown below?
Figure #7
inte
compound A
compound B
compound C
compound D
Please click here if image does not display.
Figure #8
3
203938 PPM
10
9
8
7
5
4
3
2
1
8 (ppm)
Please click here if image does not display.
O compound A
O compound D
O compound C
O compound B
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d-f
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Please don't provide handwriting solution
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How many signals are expected in the 13-C
NMR spectrum of the compound shown
below?
OH
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. Draw the structure of the compound that best fits the following 'H NMR spectrum?
CSH100
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What is the 1H NMR data (chemical shift, integration, multiplicty) of hte compound shown below?
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May you please help me with this ochem question?
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punqe
You will characterize your product by 'H NMR spectroscopy. How many different proton
environments do you expect your product compound to exhibit?
How many "C environments would you expect to see in the "C NMR spectrum?
OS IS TS ES YS SS 9S LS S 6S 09 19 19 99 59 99 L9 19 69 OL IL TL EL YL SL YL LL L 6L O1 I'8
X: parts per Million: Proton
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An unknown compound has the formula C10H12O. Elucidate its structure by scrutinizing its 1H NMR spectra, shown. Specifically, label each different type of H atom in the final structure with its NMR chemical shift in ppm.
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5
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What is the structure of the unknown? please determine it by analyzing the spectroscopic data given. thank you!
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HO
OH
36
HO
OH
Hu
350
H
5) Answer the following questions, which refer to the two diol diastereomers shown above.
a) Would you expect any difference in the number of peaks in the ¹H NMR spectra of each diol? (Y or N)
b) Would you expect any difference in the number of peaks in the ¹3C NMR spectra of each diol? (Y or N)
c) Would you expect any difference in the integral values for the peaks in the ¹H NMR spectra of each diol? (Y or N).
d) Would you expect any difference in the multiplicities for the peaks in the ¹H NMR spectra of each diol? (Y or N).
e) Would you expect any difference in the chemical shifts for the peaks in the ¹H NMR spectra of each diol? (Y or N).
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Br
CH3
Но
NH2
2
1
How many signals would you see in the 'H NMR spectrum of compound 2?
0 4
0 7
08
0 6
12
#
$4
&
18
2
3
4
6.
Q
W
R
T
Y
4
A
S
F
G
C
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Look at NMR and answer #2,3 and 4
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How many positive signals do you expect to see on the DEPT-135 13C NMR spectrumof the compound
below?
O
5
04
O 3
02
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