Fall 2000

Chemistry 118A
Student #
This exam contains 12 pages and 11 problems. When you are told to
start, check to see that all the pages are there. If not, ask for help now.
No adjustments will be made later
1. (24 pts) Matching. Each structure on the left contains a functional
group named on the right. Match them in the spaces given below.
O
A

1 alcohol

CH3CNHCH3

3 amide

CH3
B

2 aldehyde

CH3CHOCH3

Problem
1
2
3
4
5
6
7
8
9
10
11
TOTAL

Score

4 amine
5 benzene

CH3CH2NHCH2CH3

CH3C

9 haloalkane
10 ketone

CH3

11 lactone

O
E

7 ester
8 ether

CH3 O
D

6 carboxylic acid

12 nitrile

CH3COCH2CH3

13 nitrone
14 sulfone
F

CH3

15 sulfoxide

Structure A contains functional group number _______

O
G

CH3CH2CH2COH

Structure B contains functional group number _______

Structure C contains functional group number _______

Structure D contains functional group number _______

Structure E contains functional group number _______
Structure F contains functional group number _______
Structure G contains functional group number _______
Structure H contains functional group number _______

Practice Final Page 2

Chemistry 118A

Initials

2. (16 pts) Provide complete systematic (IUPAC/CA) names for each of the molecules shown below.
a.

CH3CH2CH2 CH2CH3
C H
CH2OH

CH3
b.

CH3O

Br

CH3CH2

H
CH2Cl

H
c.

Br

CH3

CH3 CH3
d.

CH3CH

CCH3
CH3

Practice Final Page 3

Chemistry 118A

Initials

3. (36 pts) Multiple choice. Circle the best answer.

a. The shapes of organic molecules are determined by
hybridization
of orbitals

electron
repulsion

resonance
hybrids

b. Contains the most electrophilic carbon

CH3

CH3

CH3

c. Best resonance form for CH3ONC

CH3O

d. Best resonance form for [CH3OC(CH3)2]

CH3O

C
CH3

Cl
C
C
H

CH3
Br

CH3

CH3

CH3

Cl

Br

Br

Br

Cl

Cl

CH3

CH3

C
CH3

e. Enantiomer of
CH3

C:

CH3

CH3

: :

CH3

CH3

: :

C:

CH3
CH3

: :

C:

: :

: :

CH3O

CH3

CH3

Practice Final Page 4

Chemistry 118A

Initials

3. (continued)
f. Most easily dehydrated
OH

OH

OH
g. Strongest acid
CH3
H2O

CF3

CH3CH2OH

CF3CH2OH

OH

C
CH3

h. Best reagent for E2 eliminations

OH

[(CH3)2CH]2N

CH3CH2O

NH2

i. Necessary to displace hydroxy group

make a
better
leaving group

use
aprotic
solvent

improve
nucleophile

increase
strength
of base

j. Reason for reactivity of oxacyclopropanes

polarity

hyperconjugation

ring strain

chirality

k. Most stable

l. Most likely to give a rearrangement product upon treatment with conc. H2SO4
CH2CH3
CH3CHCH2CH2OH

CH2CH3
CH3CH2

C
CH3

OH

CH3

CH2CH3
CH3

CH

CH
OH

CH3

CH3

C
CH3

CH2

CH2OH

Practice Final Page 5

Chemistry 118A

Initials

3. (continued)
m. Most strongly hydrogen bonded in protic solvent

Br

SCH3

Cl

n. Best solvent for SN2 reactions

O

CH3CN(CH3)2

CH3CNHCH3

CH3CNH2

NH3

O
o. Oxidation state of carbon in HCOH
2

+1

+2

+3

+1

+2

+3

O
p. Oxidation state of carbon in HCH
2

q. Compound with highest boiling point

CH3
CH3CH2CH2CH2OH

CH3COH

(CH3CH2)2O

CH3OCH2CH2CH3

CH3

r. Best retrosynthetic disconnection for

OH

CH3CH2

CH2CH2CH3

CH2CH2CH2CH2CH3

CH3CH2Br
O
CH3(CH2)2C(CH2)4CH3

CH3CH2CH2MgBr
O
CH3CH2C(CH2)4CH3

CH3(CH2)4MgBr
O
CH3CH2CCH2CH2CH3

Practice Final Page 6

Chemistry 118A

Initials

4. (10 pts) Multiple choice. Circle the correct answer.

a. Most stable carbocation
CH3
CH3+

CH3CH2CHCH2

CH3

CH3
+

CH3CH2CCH3

CH3CHCHCH3

b. Best nucleophile

(pKa of conjugate acid:

F
3.2

Cl
2.2

Br
4.7

I
5.2)

c. Best nucleophile

(pKa of conjugate acid:

CH3O
15.5

CH2S
10.0

CH3NH2
10.6

CN
9.2)

d. Fastest reaction with H2O

CH3
CH3CH2CHCH2I

CH3
CH3CH2CCH2
I

CH3
CH3CHCHCH2
I

e. Slowest reaction with H2O

CH3
CH3CH2CHCH2I

CH3

CH3
CH3CH2CCH2
I

CH3CHCHCH2
I

Practice Final Page 7

Chemistry 118A

Initials

5. (21 pts) Write the structure(s) of the major organic product(s) of each reaction below to the right of the
arrow. Then, write the abbreviation that describes the mechanism in the space provided. IF YOU THINK
THAT NO REACTION (or only an exceedingly slow reaction) OCCURS, WRITE NR. Assume all
indicated reagents are present in excess.
Mechanism
NaSH

Cl

a.

CH3OH
HO

NaSH

b.

CH3OH
Cl

H
KCN

c.

Acetone
CH3 H

Cl

CH3
CH3OH

d.

CH3 H

Cl

H
NaOCH3

e.

CH3OH
CH3 H

Cl

f.

NaSCH3
CH3

Br
H

DMSO

Practice Final Page 8

Chemistry 118A

Initials

CHOOSE ONLY ONE OF THE TWO PARTS OF THIS

PROBLEM TO DO. IF YOU WORK ON BOTH, INDICATE
WHICH ONE YOU WANT GRADED.
6. (20 pts) Formulate mechanisms to explain EITHER ONE of the two following reactions.
Your answer must be in the form of chemical equations not words.
a. Give the complete, step-by-step mechanism for the oxidation of isoborneol using CrO3 as the
oxidizing agent. Be sure to write each intermediate structure as well as the structure of the product
(which is camphor).
CH3
CH3

OH
CH3

conc.
H2SO4

CH3
b.

CH
OH

CH3

CH3

120 C
CH3

Practice Final Page 9

Chemistry 118A

Initials
CHO

7. (10 pts) Using good retrosynthetic strategy, propose a synthesis of

CH2CH3

CH2CH3
You may start with any inorganic reagents and any organic molecules you like with the restriction that no
starting material may have more than 5 carbons.

8. (15 pts) Show how you would carry out the following conversions
I

OH
a.

CH3CHCHCH3

CH3CHCHCH3
CH3

CH3

with inversion of configuration at the reacting carbon

OH
b.

CH3CHCHCH3
CH3

CH3CHCHCH3
CH3

with retention of configuration at the reacting carbon

OH
c.

CH3CHCHCH3
CH3

I
CH3C
CH3

CH2CH3

Chemistry 118A

Practice Final Page 10

Initials

9. (20 pts) Write out complete, step-by-step mechanisms and final major organic products for the reactions
O
, with each of the reagents below.
of (S)-2-ethyloxacyclopropane,
CH
3

CH2CH3

a. NaOCH2CH3 in CH3CH2OH

b. Dilute H+ in CH3CH2OH

10. (10 pts) Write a complete, step-by-step mechanism for the following reaction.

a.

conc. HI
CH3CH2OH

CH3CH2I

Chemistry 118A

Practice Final Page 11

Initials

11. (18 pts) You are given the molecular formula, NMR, and IR of two unknown compounds. Deduce their
structures.
a. The molecular formula is C4H9Cl, and the NMR amd IR are shown below.

Chemistry 118A

Practice Final Page 12

Initials

11. (Continued)
b. The molecular formula is C5H12O, and the NMR amd IR are shown below.

2
21
1

Answer

c. Show how you would convert the compound responsible for the spectra in part 'a' into the compound
responsible for the spectra in part 'b'.