Chemistry 2423

Exam 3A

Hydrocortisone- Used as an antagonist in the treatment of allergies and

inflammation

CHEM 2423 EXAM # 3A (Chapters 8-11)

Dr. Pahlavan

PART I- Multiple Choice (3 points each)

____ 1. Compounds contain two or more chiral centers, but are achiral overall, are called:
A. enantiomers compounds
C. diastereomers

B. meso compounds
D. reference compound

____ 2. How many chiral centers does the following compound have?
CH3 CHBr CHCl CH2 CH3
A. 1

B. 2

C. 3

D. 4

____ 3. Consider the following structures, identify the type of isomers.

H

CH3

H3C

Br

Br

CH3

and
H

H3C
Br

A. identical

Br

B. Constitutional isomers

C. diastereoisomers

D. enantiomers

____ 4. What is the correct absolute configuration for the following compouds?
CH3

CN

CH3CH2
H

A. R

B. S

C. achiral

D. cannot be determined

____ 5. The (+) enanthiomer of a compound has an observed optical rotation of 1.75 degrees
when measure in a one dm tube at a concentration of 0.3 g/ 15 ml. What is thespecific rotation ,
[], of the molecule?
A. 30 o

B. 45 o

C. 87.5o

D. 1.75 o

____ 6. Which of the following reagents would be used to complete the following reaction?
CH3 CH2 CH2 C C - H CH3 CH2 CH2 CH2 CHO
A. 1. BH3,THF 2. H2O2, NaOH , H2O
C. KMnO4 / H3O+

B. HgSO4, H2SO4, H2O

D. none of these
2

____ 7. What is the correct configuration for the following compound ?

CH3

Br

Br

CH3

A. (2R,3S)

B. (2S,3S)

C. (2R,3R)

D. (2S,3R)

____ 8. Identify the correct order of the following reaction mechanisms as SN1, SN2, E1, or E2
I. CH3CH2Br + H2O CH3CH2OH + HBr
II. Rate = k[RX] for this elimination reaction
III. Using Nu = Cl or I does not affect the rate of this substitution reaction
IV.
CH2Br
+ KOH

CH2
+ KBr + H2O

V. Results in inversion of configuration

A. SN2, E2, SN2, E1, SN1
C. SN1, E2, SN1, E1, SN2

B. SN2, E1, SN1, E2, SN2

D. SN1, E1, SN2, E2, SN1

____ 9. The transformation is ____________________.

CH3

CH3 - CH - CH3

A. an oxidation
C. neither an oxidation nor reduction

CH3
CH3 - C - CH3
Br

B. a reduction
D. cannot be determined

____ 10. How many allylic hydrogens does the following compound have?
CH - CH3

A. 3

B. 4

C. 6

D. 7

____ 11. Oxidation of a terminal alkyne with either O3 or acidic KMnO4 will yield
__________________________.
A. one mole of a carboxylic acid
C. both A and B

B. one mole of carbon dioxide

D. two moles of carboxylic acids

____ 12. What is the order of increasing oxidation level of the following compounds? (least oxidized to more
oxidized)
IV. CH2 = CH2
III. CH3 - CHO
II. CH3CH3
I. CH3 - COOH
3

A. I < II < III < IV B. II < IV < III < I

C. IV < III < II < I
____ 13. What is the relationship between the following compounds?
OH

D. III < I < IV < II

CH3 - C = CH - CH3

and

CH3 - C - CH2 - CH3

A. tautomers
B. enantiomers
____ 14. Which one of the following is a tertiary alkyl halide?
A. 1-chloro-2-methylpentane
C. 2-chloro-3-methylpentane

C. diastereomers

D. identical

B. 2-chloro-2-methylpentane
D. 1-chloropentane

____ 15. Alkyl halides undergo elimination of HX, dehydrohalogenation, on treatment with a _______ .
A. strong base

B. weak base

C. strong acid

D. weak acid

____ 16. A compound that possesses an internal plane of symmetry (where one half of the molecule is the
mirror image of the other half of the molecule) is __________.
A. enantiomeric

B. achiral

C. optically active

D. chiral

____ 17. The organometallic reagent R Mg X is called a

A. Gilman reagent

B. Simons-Smith reagent

C. Grignard reagent

D. Ficher reagent

____ 18. How many stereoisomers does the following compound has?
CH3

Br

OH

Br

CH3
CH3

A. 1

B. 2

C. 4

D. 0

____ 19. Which of the following represents vinylic carbocation?

CH2 - CH = CH2
I

A. I only

CH3 - CH = C - CH3

III

II

B. I and II

C. I and III

____ 20. What is the final product of the following reaction?

1) Mg/ether
2) H2O
CH3 - CH2 - CH2 Br
A. CH3 CH2 CH2OH

CH3 - CH - C

B. CH3 CH2 CH3

4

D. II only

C-H

C. CH3 CH2 CH2 Mg Br

PART II- Show your work

D. CH3 CH = CH2

21. Naming and Structures ( 8 points)

Br

H
CH3

CH3 - CH2- CH2 - CHBr - C

C -H

CH2CH3

_______________________________

__________________________________

Cis- 1-bromo-3- isopropylcyclohexane

4-chloro-2-hexyne

22. Propose a mechanism to account for the following reaction. Please show the structures of
the intermediates and using curved arrows to indicate electron flow in each step.
(Rearrangement may occur)(2points)
HBr /ether

CH3

23. Complete the following reactions. (20 points)

a) CH3 - CH2 - C

H2

C- CH3

Lindlar catalyst

b)
CH2 - C

HgSO4, H2 SO4

C-H

H 2O
C

C- H

c)

1) NaNH2
2) CH3CH2Br

d)

e)

CH3 - CH2 - C

C - CH3

KMnO4/ H3O

C- H
2 HCl

CH2-CH2OH
PBr3

f)

OH

SOCl2

g)

pyridine
CH3

h) CH3 - C = CH - CH3

Mg /ether

H2O

Br
i)

CH3 - CH2 - CH - CH2Br

CH3

1) 2 Li, pentane
2) CuI
3) CH3-CHBr
CH3

j)

Br

KOH

24. Show by a series of reactions how could you prepare the following compounds from the
indicated starting compound. Be sure to clearly indicate the reagents used in each step. ( 10 points)
( a) CH3 - C

C-H

CH3 - C

C - CH2

CH - CH3

( b)

CH3

BONUS Question(10 points)- Show all your work. (Do only one of these a or b)
a) Draw one enantiomer, and one diastereomer of the following compound.
OH
H

Br

CH3
H
CH2CH3

b) Given The MS spectrum for a compound with only one oxygen, CxHyO , answer the
following questions.

a) Determine the position of parent peak and base peak.

b) Determine the possible structure of the compound.
c) What fragment has the highest intensity?

ORGANIC CHEM 2423 EXAM #3A (Answers)

PART I- Multiple Choice (3 points each)

1. B
8. B
15. A

2. B
9. A
16.B

3. D
10. D
17.C

4. B
11. C
18. B

5. C
12. B
19. D

6. A
13.A
20. B

PART II- Show youe work (8 points)

21.
(R) 2- bromobutane

3 Bromo 1- hexyne

Br

CH3 - CH2 - CH - C

C - CH3

Cl
CH3 - CH - CH3

22.

7. B
14.B

H - Br

hydride shift

CH3

Br

CH3

CH3

23.
H

H
a)

b)

C=C

CH3

CH3-CH2
C

CH2 - C - CH3
O

C - CH2 - CH3

c)

d)

CH3 - CH2 - C -OH + CH3-- COOH

Cl
CH2 - CH2Br

C - CH3
f)

e)

Cl

g)

h)

Cl

CH3 - CH = CH -CH3

CH3
i) CH3 - CH2 - CH - CH2 - CH - CH3
CH3

j)

CH3

24.
( a) CH3 - C

CH3 - C

C-H

C -CH2

NaNH2

CH3 - C

CH2Br

C: Na

CH - CH3

(b)

CH3
Cl2
light

Cl

2 Li

CH3CH- Br
CuI

CH3

pentane

10

Br

CH3

Bonus Question (10 points) Show all your work.

a)
OH
H

CH3

Br

H
CH2CH3

b) parent peak , m/e = 84

Enantiomer

Diastereomer

OH

OH

CH3

H
Br

CH3

Br

CH2CH3

CH2CH3

base peak , m/e = 69

C5H8O , D.U. = (5) (8/2) +1 = 2 (two double bond) or one triple bond
Structure:
O

CH3 - C - CH2 - CH = CH2

m/z =84

O
C - CH2 - CH = CH2

O
m/z = 69

C - CH3

m/z =43

Chemistry 2423
Exam 3B
11

Benzylpenicillin- is a group of Beta-lactam antibiotics used in the treatment of bacterial infections

caused by susceptible, usually Gram-positive, organisms.

CHEM 2423 EXAM # 3B (Chapters 8-11)

Dr. Pahlavan

DIRECTIONS- Please answer all questions in the space provided as completely and clearly as possible .
Show all your work for the writing portions of the exam.
PART I- Multiple Choice (3 points each)
____1. Which of the following bromoalkanes is secondary alkylhalide?
H
A. CH3CH2CH2CH2Br

B. CH3CHBrCH2CH3

C. H - C - H
Br

CH3
D. CH3 - C - Br

E. CH3 CH2Br

CH3

____2. Which statement most correctly describes the rate determining step (stable intermediate carbocation) in
the reaction below?
12

Cl
CH3 - C = CH - CH2 - CH3

+ HCl

CH3 - C - CH2 - CH2 - CH3

CH3

CH3

A. Formation of a 3o carbocation
C. Formation of 3o radical
E. Addition of Cl- to a carbocation

B. Formation of 2o carbocation
D. Rearrangement of a 2o to 3o carbocation

____3. 1-Butyne (shown below) contains which of the following hybridized orbitals?
H H

H-C

C-C-C-H
H H

A. sp3 only

B. sp, sp2, and sp3

C. sp and sp3

D. sp only

E. sp2 and sp3

____4. What is the product of the following reaction?

CH3CH = CH2 + HBr
A. CH3CH2CH2Br

B. CH3 - CH - CH3

ROOR
peroxide
C. CH3 - CH - CH2Br

D. CH3CH2CH3

E. CH3 - CH - CH3
OOR

Br

Br

____5. How many sigma ( ) and pi ( )bonds are found in ethyne?

A. 2 , 2

B. 3 , 2

C. 1 , 2

D. 4 , 1

D. 1 , 1

____6. Which of the following best describes the relationship between these two compounds?
CH3
CH3
and
CH3
A. Structural isomers
D. Identical compounds

CH3
B. Enantimers
C. Diastereomers
E. Meso compounds

____ 7. According to the Cahn-Ingold-Prelog convention, what is the correct designation of the follown
stereoisomers?
Br

CH3

C
H
CH2CH3

13

A. (S)

B. ( R)

C. (R,S)

D. (Z)

E. Meso

____ 8. Which one of the following compounds below is chiral?

O

OH

B.

A.

C - CH3

C - CH3

CH3

OH

OH

HO

CH3

____ 9. What is the correct IUPAC name of the following compound?

Br

CH3 - C

C - CH2 - C - CH3
CH3

A. 5-Bromo-2-heptyne
C. 2-Bromo-2-methyl-4-hexyne
E. 5-Bromo-5-methyl-2-hexyne

B. 3-Bromo-5-heptyne
D. 5-Bromo-5,5-dimethylhexyne

____10. Which of the alkyne addition reactions below involves an enol intermediate?
A. hydroboration/oxidation
C. hydrogenation
E. both A and B

B. treatment with HgSO4 in dilute H2 SO4

D. hydrohalogenation

____11. The reagent needed to convert 2-butyne to trans-2-butene is _______________.

A. H2/Pt

B. H2/ Lindlars catalyst

C. Li/NH3

D. Na/NH3

E. both C and D

____ 12. Which of the following compounds is NOT super-imposable on its mirror image?
CH3

Br
H
A.

H 3C

CH3
CH2CH3

B.
H

OH

Cl

D.

C.
H

Cl

C6H5

CH3
Br

CH3

____13. What is the product of the following reaction?

14

E.
OH

OH

C-C-C

E.

D.

C.

CH3

CH3

OH

OH

CH3 - C
H

C=C

A.

C=C

CH3 - C

C - CH2OH

E. CH3 - C

____14. The structure

C.

CH3

D. CH3CH2CH2CO2H

CO2H

B.
CO2H

CH3

Pt

+ excess H2

C - CO2H

C - CHO

CO2H
H

OH

OH
CO2H

A. has two chiral and is optically active

B. rotates polarized light counterclockwise
C. rotates polarized light clockwise
D. has no chiral carbons
E. has a plane of symmetry and is optically inactive
____15. Which of the following represents the intermediate formed in the reaction below?
CH3

CH3
H3C - C - CH3
H
CH3
A.

H3C - C - CH3

Br2

H3C - C - CH3

uv light

Br
CH3
B. H3C - C - CH2

CH3

CH2

C. H3C - C - CH3

D. H3C - C - CH3

____16. What is the principle organic product of this reaction sequence?

CH3CH2CH2 Br
A.

CH3CH2CH3

B. CH3CH2CH2OH

CH3
E. H3C - C - CH3

Br

H2O

Mg
ether

C. CH3 CH = CH2

D.

CH3CH2CHO

E.

CH3CH2COOH

____17. What is the major product of the following reaction?

CH3 - CH = CH2
A. CH3 - CHCl - CH3

B. CH3-CHCl - CH2Cl

Cl2

CCl4

C. CH3-CH2 - CH2Cl

____18. Which of the following compound consider to be chiral?

15

D. CH2Cl -CH = CH2

E. CH3CH2CH3

OH
F
OH
C.

B.

A.

D. both A and B

Cl

E. both A and C

Br
OH

____19. A newly isolated natural product was shown to be optically active. If a solution of 2.0 g in 10 ml of
ethanol in a 50 cm tube gives a rotation of +2.57o, what is the specific rotation of this natural
product?
A. -2.57 o

B. +0.257 o

C. +2.57 o

D. +0.0257 o

E. none of these

____20. A mixtur of equal amounts of two enantiomers are _____________________.

A. is called racemic mixture
B. is optically inactive
C. implies that the enantiomers are meso forms
D. both A and B

D. none of these

PART II Show your work

16. Naming and structures ( 3 points each)
a) Give IUPAC names for the following compounds
CH3

CH

Br

CH3 - C - C

CH

CH3

Cl

II.

I.

III.

I. _______________________________________

II. _______________________________________

III. ______________________________________
b) Draw structures corresponding to the following systematic names;
(R ) 2- chlorobutane

2,5,5-trimethyl-3-heptyne

17. ( 5 points) Show by a series of reactions how could you prepare the following compounds from the
indicated starting compound. Be sure to clearly indicate the reagents used in each step.
HC

CH

CH3 - CH2 - CH - CH3

Br

16

18. ( 5 points) Propose a mechanism to account for the following reaction. Please show the structures of
the intermediates and using curved arrows to indicate electron flow in each step.
(Rearrangement may occur)
HBr /ether

CH3

19. (5 points) Give an example for the followings;

I. an enol

II. a tertiary alkyl halide

III. a terminal alkyne

IV. a chiral compound

V. a meso compound

20. Predict the major product in each of the following reactions. (2 points each)

17

CH2Br
CH3 - O

a)

CH2CH3

b)

NBS/CCl4

OH
PBr3

c)

HBr/ ether

d)

e) CH3 - CH2 - C
C

C-H

H 2O

C - CH3
1. BH3, THF

f)

2.H2O2 , OH

g)

h)

HgSO4/H2SO4

CH3 - CH2 C

C - CH3

i)

HC

j)

CH3 - CH- C

C - CH3

C - CH3

Li / NH3(liq)

2 Br2

NaNH2

C - CH3

CH2Br

KMnO4
H3O

CH3

Bonus Question ( 10 points) Please show all your work for complete credit.
18

a) Complete the following tree of reactions by giving the major products. Identify structures for compounds
A, B ,C, D, and E.
E
H2/Lindlar's
catalyst
1 - propyne

NaNH2

CH3CH2Br

1 mole Br2/CCl4

KMnO4/H3O
CH3 - CHO +

b)

compound D

Given The MS spectrum for a compound with only one oxygen, CxHyO2 , answer the following
questions.

a) Determine the position of parent peak and base peak.

b) Determine the possible structure of the compound.
c) What fragment has the highest intensity?

ORGANIC CHEM 2423 EXAM #3B (Answers)

19

1. B
12. D
16. a)

2. A
13.D

3. C
14. E

I.
I.
II.

4. A
15. A

5. B
16. A

6. D
17. B

7. B
18. C

8. B
19. C

9. E
20.D

10. E

11. E

(S) 1-Bromo-1-chloropropane
3,3-dimethyl-1-butyne or t-butyl acetylene2-Ethyl-1-pentene
phenyl acetylene or ethynyl benzene

b)
Cl

CH3

C - C - CH2 CH3

CH3 - CH - C

CH2CH3

CH3

CH3

CH3

17.
HC

CH3 - CH2 - CH - CH3

CH

Br

NaNH2
CH3CH2Br
CH3- CH2 - C

CH3CH2

H2

C- H

HBr/ether
H
C = C

Lindlar's catalyst

18.
H - Br

hydride shift

CH3

Br

CH3

CH3

19. Student answers varies

I. CH3 - C =CH2

II.

III.

CH3 - C -Cl

CH3 - C

V.

OH

IV.

C -H

CH3

H
Cl

20.
CH2CH3

a)

OR

b)

Br

CH-CH3
c)

Br

Br
d)

Br
O
O

e) CH3 - CH2 - C - CH3

CH2 - C - CH3
f)

CH3

C - CH2 - CH3

C=C
g)

or

H
O

h) CH3 - CH2 - CBr2 - CBr2 - CH3

i) CH3 - C

C - CH2 -

j) CH3 - CH - C
CH3

20

OH

OH
CH3

CH3

CH2OCH3

CH3

CH3

CH3

OH

Br

O
+

OH

CH3 - C
OH

Bonus Question
a)

Br
C: Na )

A (CH3 - C

B ( CH3 - C

C - CH2 - CH3 )

O
)

D ( CH3 - C
H

E. (

C=C
CH3

b) parent peak , m/e = 84

C(

CH2CH3
)

C=C
CH3

Br

CH2CH3

base peak , m/e = 43

DU = (4) (8/2) +1 = 1 db (C=O)

.
Fragments appear due to bond cleavage next to C=O (alkyl loss, OCH2CH3 = 45 and CH3CO+ = 43) and
hydrogen rearrangements.

Structure:

C4H8O2, MW = 88.11, Ester - Ethyl acetate

O

CH3 - C - O - CH2 - CH3

21