CHEMISTRY 2411

NAME_________________

EXAM IIA - Key

Fall, 2012
Kirberger

All notes, books, etc., must be placed out of sight. Please read each of the problems carefully. If
something is not clear, please ask.
The exam is worth a total of 112 points. Make sure your exam is complete.
Answers should be placed in the space provided. Write legibly--if I cannot read it--it is wrong.
Please include an explanation whenever asked to or whenever necessary to make your answer
clear. Please put your name on every page of the exam.
As usual, no cheating is allowed. Good Luck!!!

Chemistry 2411

Exam IIA

Name ___________________________ 2

1) (4 Points each) Name each of the following compounds.

a.

b.

bicyclo[4.4.2]dodecane

3,4-diethyl-2-methylhexane

c.

d.

5-tert-butyl-4-isopropyl-2-methyloctane

trans-1-ethyl-2-methylcyclopentane

e.

f.

Br

Cl

4-bromo-2-chloro-1-cyclopropylcyclohexane
g.
h.

Br

Br

1,3-dibromo-6-ethylcyclodecane

4-sec-butyl-3,7-diethyl-6-isobutyl-2,8-dimethylnonane 7-ethyl-2,3,6-trimethyl-5-(3-methylbutyl)nonane

Chemistry 2411

Exam IIA

Name ___________________________ 3

2) (4 Points each) Draw each of the following compounds using skeletal structures.
a. 2-fluoro-3,4,5,6,7-pentamethyloctane

b. 4-sec-butyl-2-chloro-5-methylheptane
Cl

c. cis-1-ethyl-3-methylcyclohexane

d. 5-(2-bromobutyl)-8-chloro-3,4-dimethyldecane
Cl

Br

e. 4-isopropyl-2,3,5,6-tetramethylheptane

f. cyclopentylcyclohexane

Chemistry 2411

Exam IIA

Name ___________________________ 4

3) (4 Points) A compound has the empirical formula C8H16. Is this an alkane? If it is not an alkane,
what other classification(s) of hydrocarbon might it fall under?

Answer: No. Could be alkene or cycloalkane.

4) (4 Points) Which of the following reactive intermediates can act as either an electrophile or a
nucleophile?
A) carbanions
B) carbocations
C) carbenes
D) free radicals
E) alkanes
Answer: C
5) (8 Points each) Draw the conformational analysis of butane along the C2-C3 axis. Draw
Newman projections for each of the 4 major conformations from 0-180. Label each of the
conformations, and plot the relative potential energy levels for each conformation.
Answer:

Chemistry 2411

Exam IIA

Name ___________________________ 5

6) (4 points) Given a Keq of 2.2 at 25C, calculate the corresponding G in kJ/mol. [R = 8.314
JK-1 mol-1]
Answer: -2.0 kJ/mol

7) (4 Points) Which of the presented mechanisms would be the most energetically favorable and
thus the most likely mechanism to actually occur for the following free radical chain reaction?
(bond dissociation energies -- H-H = 104 kcal/mol; Cl-Cl = 58 kcal/mol; H-Cl = 103 kcal/mol)
H2 + Cl2
A) H2

2 HCl
H + H

H + Cl2 Cl + HCl
H + Cl HCl
B) Cl2
Cl + Cl
Cl + H2 H + HCl
H + Cl2 HCl + Cl
C) H2

H + H

H + Cl2 Cl + HCl
Cl + H2 HCl + H
D) Cl2

Cl + Cl

Cl + H2 H + HCl
H + Cl HCl
Answer: B

Chemistry 2411

Exam IIA

Name ___________________________ 6

8) (4 Points each) Consider the one-step conversion of F to G. Given that the reaction is
endothermic by 5 kcal/mol and that the energy difference between G and the transition state
for the process is 15 kcal/mol, sketch a reaction-energy diagram for this reaction. Make sure
to show how the given energy differences are consistent with your sketch.
Answer:

9) (4 Points) Consider the bond dissociation energies listed below in kcal/mol.

CH3-Br
CH3CH2-Br
(CH3)2CH-Br
(CH3)3C-Br

70
68
68
65

These data show that the carbon-bromine bond is weakest when bromine is bound to a ________.
A) methyl carbon
B) primary carbon
C) secondary carbon
D) tertiary carbon
E) quaternary carbon
Answer: D
10) (4 Points) How many distinct monochlorinated products can result when isobutane is
subjected to free radical chlorination?
A) 1
B) 2
C) 3
D) 4
E) 5
Answer: B

Chemistry 2411

Exam IIA

Name ___________________________ 7

11) (4 Points) Rank the free radicals (I-III) shown below in order of decreasing stability (i.e., from
most stable to least stable).

A) I > III > II

B) II > III > I
C) I > II > III
D) II > I > III
E) III > II > I
Answer: A
12) (4 Points) Draw the 3 monochlorination products expected from reaction of chlorine with
3,4-dimethylhexane. Circle the major product (hint: this is a radical reaction).

Answer:

13) (4 Points) Comparing n-hexane with 3-ethyl,2,4-dimethylpentane, which would have the
higher boiling point and why?
3-ethyl-2,4-dimethylpentane (136 C) has more carbon atoms than n-hexane (69 C)

14) (8 Points) Draw the most stable conformation for the compound 2,4-diethyl-1,2-dimethyl-4propylcyclohexane (hint: draw the skeletal structure first, then explore the conformations).

Chemistry 2411

Exam IIA

Name ___________________________ 8