organic chem final

Topics: Chemistry, Chemical compound, Nucleophilic addition Pages: 55 (2002 words) Published: December 6, 2013
Chemistry 213a Final Exam, Fall 2007

Code 111

Page 1

Please ensure that you have entered code 111 on your answer sheet.

Questions 1 and 2 refer to the compound on the right,
simvastatin, a drug used for the treatment of high
cholesterol.

HO
O

O
1.

O

What is NOT correct about simvastatin?

H

A) It contains a conjugated diene
B) It contains a primary alcohol
C) It contains an ester and a lactone
D) It contains a secondary alcohol
E) It contains a quaternary carbon atom

2.

Simvastatin contains how many non-bonding electron pairs, and how many sp2-hybridized carbon atoms?

Non-bonding pairs

sp2 carbon atoms

A)

10

6

B)

10

4

C)

6

6

D)

6

2

E)

8

4

O

Chemistry 213a Final Exam, Fall 2007

3.

Page 2

Which one of the following is the most stable?

A)

D)

4.

Code 111

O

NH2

B)

O
H 2C CH

O
E)

OH

What is a proper IUPAC name for the following compound?
Cl

A) 4,4-dimethyl-5-tert-butyl-8-chlorononane
B) 5-tert-butyl-2-chloro-6,6-dimethylnonane
C) 5-sec-butyl-8-chloro-4,4-dimethylnonane
D) 8-chloro-5-isopropyl-4,4-dimethylnonane
E) 5-sec-butyl-2-chloro-6,6-dimethylnonane

5.

C)

How many constitutional isomers exist for C4H9Br?
A) 3
B) 4
C) 5
D) 2
E) 6

Chemistry 213a Final Exam, Fall 2007

6.

Code 111

Page 3

Which one of the following is shown in its most stable conformation?

CH3
A)

H

OH

H

OH

C(CH3)3
B)
Cl

CH3
H
H

Br

C)

D)
H

Br
H

HOH2C
HO
HO

O
OH
OH

Cl
H

Cl

E)
H

Cl
H

7.

Which one of the following has the greatest number of cis/trans isomers?

A) 1,2-dimethylcyclohexane
B) 3,4-dichlorocyclopentene
C) 2,4-heptadiene
D) 3-methylcyclopentane
E) 1,3-butadiene

Chemistry 213a Final Exam, Fall 2007

8.

Code 111

Page 4

The two products formed in the reaction below can be correctly described as? HCl

products

1. Constitutional isomers
2. Regioisomers
3. Stereoisomers
A) All of 1, 2, and 3
B) 1 only
C) 2 and 3 only
D) 2 only
E) 1 and 2 only
9.

Terpin is prepared commercially by the acid-catalyzed hydration of limonene. What is the structural formula of terpin?

+ 2 H 2O

H2SO 4

C10H20O
Terpin

OH

OH

OH
A)

B)

C)
OH

OH
HO
OH

OH
D)

E)
OH

OH

OH

OH

Chemistry 213a Final Exam, Fall 2007

10.

Code 111

Page 5

How many stereocentres are present in the antibiotic erythronolide B?

H 3CH2C
A) 7

CH3

O

CH3

B) 10

O
H3C

C) 11

CH3 OH

O

D) 12
HO

E) 8

CH 3
OH

HO

11.

CH3

If the indicated carbon atoms in the molecule shown below are stereocentres, assign R/S configurations to them.
1
O

H
2

H

NH2
3

HO
H

H
OH
CH2OH

1

2

3

A)

not a stereocentre

R

R

B)

not a stereocentre

R

S

C)

not a stereocentre

S

R

D)

S

S
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