Spring 2015 Final Exam Review

1. What is the multiplicity expected in the hydrogen NMR spectrum for the
hydrogen atoms marked by a "star" in the following compound?

A)
B)
C)
D)

Singlet
Triplet
Quartet
Sextet

2. Rank the following alcohols from most acidic to least acidic.

A)
B)
C)
D)
E)

I>II>IV>III
II>III>IV>I
III>IV>II>I
IV>III>I>II
IV>I>III>II

3. Predict the product of the following reaction:

a.

b.

c.

d.
4. Predict the product

A)
B)
C)
Disclaimer: This is not meant to be representative of what your exam will be like. This
is simply a review your loving TAs put together for you.

Spring 2015 Final Exam Review

5. Arrange the following compounds in order of decreasing chemical shift for the
underlined hydrogens (higher ppm to lower ppm).
CH3CH2CH3
A)
B)
C)
D)

b>c
b>c
c>b
c>b

>
>
>
>

a
a>d
d>a
a>d
d>a

CH3OCH2CH3

Cl2CHCH2CH3

ClCH2CH2CH3
d

6. Choose the best reagent set for achieving the following

transformation.

A)
B)
C)
D)

PCC
Na2Cr2O7, H2SO4, H2O
KMNO4
All of the above

7. Which of the following molecules can NOT decarboxylate?

A) A only
B) B only
C) C only
D) Both A and B
8. Which reagent(s) should you use to accomplish the following
transformations?

A)

B)

C)

D)

NaBH4 then
excess

NH3,

Spring 2015 Final Exam Review

9. How many signals would the following molecule show in its 1H NMR
spectrum?

a.
b.
c.
d.

5
1
6
8

10.What is the product of the following reaction?

A)

B)

C)

D)
11.Which set of reagents is appropriate to convert the benzyl bromide to the
corresponding carboxylic acid?

A) Mg, Et2O then CO2 then H3O+

Na2Cr2O7

B) NaCN then H3O+

c) a or b

d.

12.Which reagent(s) should you use to complete the following transformation?

A) OsO4
B) Acid, methanol
C) Williamsons reagent

Spring 2015 Final Exam Review

D) NaOMe, MeOH
13.An unknown molecule A has 4 signals in the 1H NMR spectrum. Which of the
following corresponds to molecule A?
a.
b.
c.
d.

14.Which of the following ethers cannot be prepared by a Williamson ether

synthesis?
A) tert-butyl phenyl ether
B) isopropyl methyl ether
C) anisole
D) tert-butyl methyl ether
15.What is the product when the following lactone is treated with aqueous
sodium hydroxide?

a.

b.

c.

d.

16.Which is the strongest reducing agent?

A) PCC
B) KMnO4
C) NaBH4
D) LiAlH4

17.Propose a structure for the following compound.

1
H NMR spectrum of C5H8O2:
1.90 (multiplet, 4H); 2.40 (triplet, 2H); 4.26 (triplet, 2H)
a.
b.
c.
d.

Spring 2015 Final Exam Review

18.Synthesis of hexane-3,4-diol from (E)-3-hexene can be accomplished in two

ways:
i. OsO4 hydroxylation
ii. C6H5CO3H epoxidation followed by NaOH expoxide ring opening
Which of the following statements about the products from these reactions is
correct?
A) the two methods give the same product
B) (a) gives a chiral isomer, (b) gives an achiral isomer
C) (a) gives an achiral isomer, (b) gives a chiral isomer
D) two different isomers are formed, but both are chiral
19.Which of the following carboxylic acid derivatives is most difficult to
hydrolyze?

a.

b.

20.Which compound is the most basic?

A)
B)
C)

c.

d.

D)

21.How many tautomers can you draw for the following diketone?

A)
B)
C)
D)

1
2
3
4

22.Which set of reagents would accomplish the following transformation?

A) OsO4, then IO4

B) O3, then H2O2

C) mCPBA (2 eq)

D) PCC

Spring 2015 Final Exam Review

23.Which of the following is a D-ketopentose.

A)
B)
C)
D)
E)

I
II
III
IV
I and III

24.What is the product of the following reaction?

A)

B)

C)

D)

25.What is the final product of the following reaction?

a.

b.

c.

d.

26.Which conditions will give you exclusively the following compound from Dglucose?

A) MeI, NaOH
B) MeOH, HCl
C) NaOMe, MeOH

Spring 2015 Final Exam Review

D) MeI, pyridine

27.Which pi-bond will be reduced first when treated with H2(g) and Pd0?
A)
B)
C)

28.Which set of reagents would accomplish the following transformation?

A)
c

B)

C)

D) both b and

29.Choose the reagent(s) to accomplish the following transformation:

A) MgBrCH3, CO(g)
B) Sharpless dihydroxylation
C) NaCN, then acid
D) LiAlH4, PCC
30.Give the major product of the following reaction.

a.
d.

b.

c.

31.Which is the correct product?

A)

B)

C)

D)

Spring 2015 Final Exam Review

32.Identify the -linked disaccharides.

A)
B)
C)
D)
E)

I
II
IV
III and IV
I and II

33.Acid chlorides are especially useful for:

A) nucleophilic acyl addition reactions
B) electrophilic acyl addition
reactions
C) nucleophilic acyl substitution reactions D) electrophilic acyl substitution
reactions
34.What starting material is required for the following reaction?

a.
d.

b.

35.Which of the following can be identified as anomers?

A)
B)
C)
D)
E)

I and II
I and III
I and IV
II and III
III and IV

c.

Spring 2015 Final Exam Review

36.Acids can be converted to primary amines by:
A) conversion to the nitrile followed by treatment with LiAlH 4
B) conversion to the diazonium salt followed by treatment with NaBH 4
C) conversion to the primary amide followed by treatment with LiAlH 4
D) both A and B
E) Both A and C

37.

What is the product of

the following sequence:

38.Which two of the following compounds are reduced to the same chiral alditol
by sodium borohydride?

Spring 2015 Final Exam Review

A)
B)
C)
D)

I and II
II and III
III and IV
II and III

39.Predict the major products of the following reaction:

A)
C)
40.How would you make this?

B)
D)

A.) 1. NH3, HCN

2. H3O+, H2O, heat
3. NaOH
4. Neutralize
B.) 1. NH3
2. H3O+, H2O, heat
41.Which of the following compounds corresponds to the IR spectrum shown
below?

Spring 2015 Final Exam Review

42.The following transformation can be accomplished with the use of which of

the reagents below?

A)
B)
C)
D)

H2N-NH2, DCM
NH3, H2O
NH3, MeOH
Me2NH, DCM

43.Which of the following compounds corresponds to the 1HNMR spectrum

below?

Spring 2015 Final Exam Review

44.Which compound is the product of an aldol condensation?

45.What would be the product of the following reaction?

Spring 2015 Final Exam Review

46.Propose a synthesis for the following:

47.Propose a synthesis for the following:

(3 steps)

48.Propose a synthesis for the following:

49.Propose a synthesis for the following:

Answers:

Spring 2015 Final Exam Review

1. C
2. E
3. B
4. A
5. B
6. A
7. B
8. B
9. A
10.C
11.C
12.B
13.C
14.A
15.D
16.D
17.D
18.C
19.B
20.A
21.C
22.B
23.A
24.B
25.D
26.B
27.D
28.B
29.C
30.B
31.A
32.E
33.C
34.C
35.A
36.E
37.C
38.A
39.B
40.A
41.A
42.D
43.E
44.A
45.B

Spring 2015 Final Exam Review

46.

47.

Spring 2015 Final Exam Review

48.

49.

50.?