Final Exam, Chem 2210 (Organic Chemistry Lecture).

-- Answer All Questions -- Fall 1999 *A*

1.

For the molecule shown, what are the hybridization of the oxygen atom and the approximate
C-C-O bond angle, respectively?
CH 3 CH 2 CCH 2 C

CH

A. sp3 , 109.5
2.

B. sp3 , 120

C. sp2 , 120

D. sp2 , 180

What functional group is present in the molecule shown?

O

A. alcohol
3.

B. ester

C. amide

D. ether

What is the IUPAC name of the compound shown?

OH
Br
Br

A.
B.
C.
D.
4.

The most stable conformation of cis-2-tert-butylcyclohexanol is a chair with the OH group:

A.
B.
C.
D.

5.

3,3-dibromo-6-ethyl-5-methyl-7-octanol
6,6-dibromo-3-ethyl-4-methyl-2-octanol
5,5-dibromo-2-ethyl-1,3-dimethyl-1-heptanol
2-ethyl-1,3-dimethyl-5,5-dibromo-1-heptanol

equatorial and the tert-butyl group equatorial

axial and the tert-butyl group axial
equatorial and the tert-butyl group axial
axial and the tert-butyl group equatorial

What are the configurations of the carbons 1 and 2 in the compound shown?

H
H3 C

A. 1R, 2S

B. 1S, 2R

H
OH

C. 1R, 2R

D. 1S, 2S

6.

Which of the following alkyl halides gives only one alkene as the product in the E2
reaction?
Br
Br
Br

Br

A.

CH 2CCH3

B.

C. CH3CH2CCH3 D.
CH3

CH 3

7.

What is the name of the alkene shown?

H

CH 3
C

Cl

A.
B.
C.
D.
8.

CH 3

CH 2 CHCH 3

(Z)-1-chloro-2,4-dimethyl-1-pentene
(E)-1-chloro-2,4-dimethyl-1-pentene
cis-1-chloro-2,4-dimethyl-1-pentene
trans-1-chloro-2,4-dimethyl-1-pentene

What is the major organic product of the following reaction?

liquid NH
H3 CC

A. H3 CC

CCH3

C Na

H3 C

C.

B. H3 CC

D.

C
H

CCH 2 Na

H3 C

CH 3
C

+ Li

H
C

C
CH 3

CH 3

9.

What is the major organic product of the following reaction?

+

H 3 O, catalyst

(H 3 C)2 CCH2 CH 3

heat

OH

A. (H 3 C) 2 CCH 2 CH 3

B. (H 3 C) 2 C = CHCH 3

H
CH 3

C.

H2 C

D. (H 3 C) 2 CHCH = CH 2
CH 2 CH 3

10.

What is the major organic product of the reaction shown?

2 mol HBr
CH3 C

A.
B.
C.
D.
11.

CH

BrCH2 CH2 CH2 Br

CH3 CBr2 CH3
CH3 CH2 CHBr2
CH 3 CHBrCH 2 Br

What is the major organic product of the reaction shown?

C C H

Hg2+ , H2 O
H2 SO4

A.

CH 3

OH

H
C

C.

B.

D.

C
OH

C H 2C
H

12.

Which of the following reacts with [Ag(NH3 )2 ]OH giving a white precipitate?
CHCH 3

A. CH 3 CH 2 CH
C. CH 3 CH 2 C

13.

A. CH3 C

D. CH 3 CH 2 CH 2 CH 2 OH

CH

H + NH

CNH 2 B. CH3 C

C. CH3 C

CNH 3

D. CH3 C

Which of the compounds below is the best set of starting materials for the synthesis of the
compound shown?
O

15.

CCH

What is the major organic product of the reaction shown?

H 3C

14.

B. CH 3 CH 2 C

A.

Br

B.

Na

C.

Na

D.

Br

CH

and
+ -

+ -

2 CH 3

CH
and
and

O
and

CH

3 CH 2 O

CH
CH

Na

3 CH 2 Br

3 CH 2 O

Na

3 CH 2 Br

Which of the following will give the transformation shown?

+ ? ----->

A.
B.
C.
D.

Cl2 , H2 O
PBr3 followed by H3 O+
Hg(OAc)2 /H2 SO 4 , water
BH 3 , THF followed by H2 O2 , OH-

H
OH

16.

Which of the following reactions proceeds through a free radical mechanism?

(H3C)2CBrCH2CH3

A. (H3C)2CHCH = CH2 + HBr

(H 3 C) 2 CHCHBrCH 2 Br

B. (H 3 C) 2 CHCH = CH 2 + Br 2

C. (H 3 C) 2 CHCH = CH 2 + HBr

ROOR

(H 3 C) 2 CHCH 2 CH 2 Br

(H3C)2CHCHCH2Cl

D. (H3C)2CHCH = CH2 + Cl2 + H2O

OH
17.

The number of products that forms in the following reaction is ________; and the number
of pairs of enantiomers formed is __________.
CH3
Br

light

+ Cl2

ClH2C
H
A. 2; 0
18.

C. 4; 0

D. 4; 1

Which of the step(s) of a free radical chain reaction have an activation energy equal to zero?
A.
B.
C.
D.

19.

B. 3; 0

initiation only
propagation only
termination only
both termination and initiation

Which of the following molecules contains seven hydrogen atoms?

A.

OH
Cl

B.

OH
Cl

C.

O
Cl

D.

O
Cl

20.

How many sigma bonds are present in the following molecule?

A. 3
21.

B. 12

C. 15

D. 7

Which of the following compounds has the HIGHEST boiling point?

A.

22.

B.

C.

D.

What is the IUPAC name of the compound shown?

H
OH
CH3
H
A.
B.
C.
D.

23.

trans-2-methylcyclohexanol
cis-2-methylcyclohexanol
trans-1-methyl-2-cyclohexanol
cis-1-methyl-2-cyclohexanol

Which of the following statements is true about the reaction shown?

CH2 CH2 Cl
H

OCH3

OH-

CH3
A.
B.
C.
D.

The product will have R configuration.

A meso compound is produced.
The product will have S configuration.
The reaction will happen with racemization.

24.

Which of the following gives no reaction?

_
A. CH 3 + C6 H5 NH 2
B. CH3 CH2_ + CH OH
3
_
C. OH

+ CH4

_
D. OH + CH3 COOH
25.

Which of the following is the LEAST soluble in water?

A. CH3 CH2 OH

26.

B. CH 3 COOH

D. CH 3 CH2 OCH 2 CH3

Which of the following is a propagation step?

A. RO + RO
B. Br 2
C.

D.

27.

C. CH3 COCH 3

ROOR

heat

2Br

+ Br

+ HBr

+ Br

Br

Which of the following is a pair of resonance structures?

A.

B.
O

C.

D.

OH

28.

For the following structure, there are _____ 1, _____ 2, and _____ 3 hydrogens.

A. 9, 6, 3
29.

30.

C. 6, 6, 3

D. 6, 8, 2

Which of the following structures is 2-tert-butylbicyclo[2.2.0]hexane?

A.

B.

C.

D.

What is the IUPAC name for the molecule shown?

Cl

A.
B.
C.
D.
31.

B. 9, 8, 2

cis-1,2-diethyl-1-chloro-2-methylethene
E-3-chloro-4-methyl-3-hexene
E-1-chloro-1-ethyl-1-pentene
Z-1-chloro-1-ethyl-1-pentene

What are the major organic products of the reaction shown?

CCl4
+ Br2 -------> ?

Br H3 C

Br

Br

CH3

Br

Br
I

A. I and III

II
B. I and IV

H3 C
Br
III

C. II and III

D. II and IV

Br

Br

CH3
IV

32.

What is(are) the major organic product(s) of the reaction shown?

CH3 CH2 CH2 CH2 CH2 ONa + CH3 CH2 CH2 CH2 Br -----> ?
A.
B.
C.
D.

33.

CH3 CH2 CH2 CH2 CH2 OCH 2 CH2 CH2 CH3

CH3 CH2 CH2 CH2 CH2 OCH(CH 3 )CH2 CH3
CH3 CH2 CH2 CH2 CH2 OH + CH3 CH2 CH=CH 2
CH 3 CH2 CH2 CH=CH 2 + CH3 CH2 CH2 CH2 OH

Which of the following free radicals is the MOST stable?

A.

B.

C.

D.

34.

Which of the following compounds is NOT a product of the reaction shown?

CH3
H
H3 C

H
Br2
CH3 -------> ?
light
H

H
CH3
CH3
H

CH3
Br

A. H3 C
H

Br

CH3 B. H3 C
H
H

CH2 Br C. H3 C
H
H

CH3
35.

CH3

CH3

CH3
Br
CH3
H

CH2 Br

What is the direction of the dipole moment in the molecule shown?

H
H
C
H

A.

Cl

B.

C.

D.

H
D. Br

Br
CH3
H

H
CH3

36.

What is(are) the product(s) of the acid-base reaction shown?

O
+ BF3

O
A.

+ HBF3

O BF3

B.

O
C.

+ HBF3

O
D.

BF3

37. Which of the following pairs of structures are two drawings of the same compound?
H
Br

A.

C
C H3

B.

CH 3

CH3

Cl

Cl

Br

Br

CH3

Cl
H

C H2OH

HO

OH

HO

OH

CH2 OH

C H2OH

OH
D.

CH 3
C

Br

H
CH2 OH

C.

CH3

Cl

OH
H

H
OH

OH

H
H

38.

Which of the species below is an intermediate in the reaction shown?

H2 SO 4
CH3 CH2 CHCH 3 ----------> CH3 CH CHCH 3 + H 2 O
heat
|
OH
A.

..
CH3 CH2 CHCH 3

B.

CH3 CH2 CHCH 3

C.

CH3 CH2 CHCH 3

D.

39.

..
CH3 CHCHCH 3
|
OH

What is the major organic product of the following reaction?

CH CH3
CH3
Br
A.

CH CH3
CH3
Br

B.

C CH3
CH3

C.

CH CH3
Br CH3
Br

D.

C CH3
CH3

HBr

no peroxides

40.

Which of the species below is an intermediate in the reaction shown?

+ Br2

Br

H2O

+ HBr
OH

41.

A.

Br

B.

C.

O H

D.

Br

Which of the following compounds is soluble in concentrated sulfuric acid, decolorizes

bromine in carbon tetrachloride, and gives a white precipitate with silver nitrate in ammonia,
but does not give a precipitate with silver nitrate in alcohol?
A.
B.
C.
D.

42.

CH3 CH2 CH2 CH=CH 2

CH3 CH(Cl)CH2 CH=CH 2
CH3 CH2 CCCH3
CH 3 CH2 CH2 CCH

Which of the following sets of reagents can be used to bring about the transformation
shown?

?
CH

CH

CH2

CH3
A.
B.
C.
D.

H2 O, H3 O+
Hg(O 2 CCH3 )2 , H2 O; then NaBH4 , NaOH
CrO3 , H2 SO 4
BH 3 -THF; then H2 O2 , NaOH

OH
CH

CH3

CH

CH3

43.

Which of the following is the best synthesis of the compound shown?

CH3 CH CH2CH3
OCH2CH3

A. CH3 CH CH2CH3 + CH3CH2ONa

Br
B. CH3 CH CH2CH3 + CH3CH2ONa
OH
C. CH3 CH CH2CH3 + CH3CH2Br
ONa
D. CH3 CH CH2CH3 + CH3CH2OH
ONa
44.

Calculate the heat (enthalpy) of reaction for the following reaction from the given bond
dissociation energies (DH o ). All values are in kcal/mole. (CH 3 CH2 -H = 98, CH 3 CH2 -I =
53.5, CH3 CH2 -OH = 91.5, CH3 CH2 O-H = 103, H-OH = 119, H-I = 71, I-I = 36)
CH3 CH2 I + H2 O ------> CH3 CH2 OH + HI
A. 1.5 kcal/mole

B. + 1.5 kcal/mole

C. 10 kcal/mole

D. + 10 kcal/mole

45.

What is the major organic product of the reaction shown?

CH 2CH3
+ Br 2

CH2C H2Br
A.
Br
B.

CHC H3

CH2C H3
C.

Br
CH2C H3

D.
Br

46.

Which of the species below is an intermediate in the reaction shown?

CH3 CHCH
|
CH3

peroxides
CH 2 + HBr -------------> CH3 CHCH 2 CH2 Br
|
CH3

A. CH3 CHCH 2 CH3

|
CH3
B. CH3 CHCHCH 2 Br
|

CH3
C. CH3 CHCH 2 CH2
|
CH3
D. CH 3 CHCHCH 2 Br
|
CH3

47.

Which of the following is a 3 amine?

CH 3
A.

CH 3 -C-CH 3

B. CH 3 -C

CH3

NH 2
N

CH3
D. CH3 (CH2 )12 NHCH 3

C.

48.

CH3

Which of the reagents listed below would serve as the basis for a simple chemical test to
distinguish between the compounds shown?
CH3 CH2 -O-CH 2 CH3

and

CH 3 CH2 CHCH 3
Br

A.
B.
C.
D.
49.

AgNO3 in ethanol
NaOH in water
Br2 in CCl4
KMnO4 , cold

Which of the following species have a bent structure?

I. H-CC-H
A. I and III

50.

II. HOH

B. II and III

III. CH2 Cl2

C. I and IV

IV. ClNO

D. II and IV

Which of the following is an s orbital? Nuclei are indicated by solid dots, and the signs of
the wave functions are shown.

+
A.

B.

C.

D.