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CHEMISTRY 1152
EXAM IIA
Fall, 2011
Kirberger
NAME_________________
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 consists of 31 problems worth 3 points each and 1 problem worth 9 points for a total of 102 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 1152
Exam IIA
Name ________________________________
1. (3 points) Which of the following compounds is correctly classified as a tertiary alcohol?
a. 2-methyl-2-butanol
b. 2-methyl-1-butanol
c. 3-methyl-2-butanol
d. 3-methyl-1-butanol
ANS: A
PTS:
3
2. (3 points) Which compound would be the most soluble in water?
a. CH3OCH2CH2CH3
b. CH3CH2CH2CH2CH3
c. CH3CH2CH2CH2OH
d. CH3CH2OCH2CH3
ANS: C
PTS:
3
3. (3 points) Which of the following compounds would you expect to be foul smelling?
a. CH3CH2CH2OH
b. CH3CH2CH2SH
c. CH3CH2CH2CH3
d.
ANS: B
PTS:
3
4. (3 points) The boiling points of aldehydes and ketones differ from those of alcohols and alkenes due to:
a. Hydrogen bonding between like molecules (aldehyde with aldehyde)
b. Hydrogen bonding with water
c. Polar bonding between like molecules (aldehyde with aldehyde)
d. Both b and c
e. Both a and c
ANS: D
PTS:
3
5. (3 points) Place the following structures in order from lowest to highest boiling point (Ex. X < Y < Z).
a.
b.
O
HO
H3C
CH3
CH3
H3C
CH3
c.
d < c< b <a___________
d.
H3C
O
CH3
CH3
H3C
Chemistry 1152
Exam IIA
Name ________________________________
6. (4 x 3 points) Draw each of the following structures:
A.
3-chloro-1-ethoxybutane
B.
p-phenylbenzaldehyde
O
H
Cl
H3C
C.
O
CH3
3-methyl-2,4-pentanediol
D.
3-(fluoromethyl)-2-pentanol
OH
CH3
H3C
H3C
CH3
OH
F
OH
7. (6 x 3 points)
CH3
Name each of the following using correct systematic names.
A. 3-phenylcyclopentanol
B. 1,2,3-propanetriol
OH
OH
HO
C. diethylether or ethyl ethyl ether
OH
D. 1,4-dichloro-2-hexanone
O
H3C
H3C
O
Cl
CH3
Cl
E. 2-bromobutanal
F. 3-ethyl-2-pentanone
O
H
H3C
CH3
O
CH3
CH3
Br
Chemistry 1152
Exam IIA
Name ________________________________
8. (7 x 3 points) Complete the following reactions. If no reaction occurs, write “No Reaction”.
a)
H3C
+
OH
HO
CH3
H2SO4
CH3
H3C
o
140 C
CH3
CH3
O
CH3
HO
+
H
CH3
b)
CH3 CH3
H3C
H2SO4
H3C
CH3 CH3
H3C
CH3
180 oC
OH
H3C
HO
+
CH3
H
c)
CH3
HO
CH3
H3C
+ (O)
No Rxn
CH3
d)
H
O
HO
O
+ (O)
H3C
CH3
H3C
CH3
e)
CH3
CH3
CH3
H3C
+ (O)
CH3
H3C
+
HO
H
O
OH
f)
H
H3C
O
O
+
H
H+
H
HO
O
CH3
H3C
H3C
g)
O
CH3
H
OH
O
OH
H
+
2 H3CCH2-OH
Chemistry 1152
Exam IIA
Name ________________________________
9. (4 x 3 points)Identify each of the following as either (a) acetal (b) hemiacetal (c) ketal (d) hemiketal or (e) none
H3C
H3C
H3C
H3C
O
O
O
OH
OH
O
CH3
_e__
H3C
OH
H3C
O
_c__
CH3
H
H3C
CH3
O
O
CH3
CH3
_a__
CH3
__d__
OH
O
H 3C
H
10. (3 points) This compound
a. Benedict’s reagent
b. Tollens’ reagent
c. Neither
d. Both
ANS: D
PTS:
would be expected to react with:
3
11. (3 points) To what characteristic(s) do aldehydes and ketones owe their ability to form hydrogen bonds?
a. having a doubly bonded oxygen
b. possessing an oxygen instead of an interior carbon
c. hydrogen on the adjacent carbon
d. all of the responses are correct
ANS: A
PTS:
3
12. (3 points) The boiling points of aldehydes and ketones differ from those of alcohols and alkenes due to:
a. Hydrogen bonding between like molecules (aldehyde with aldehyde)
b. Hydrogen bonding with water
c. Dipolar bonding between like molecules (aldehyde with aldehyde)
d. Both b and c
e. Both a and c
ANS: D
PTS:
3
13. (3 points) Assuming that molecular weights are comparable, which of the following compounds would you expect to
have the highest boiling point?
a. aldehyde
b. alkene
c. alcohol
d. ketone
ANS: C
PTS:
1
Chemistry 1152
Exam IIA
Name ________________________________
14. (9 points) Two products in addition to water are formed in the following reaction. Draw (3 points) and name the
products (3 points), and explain why one is the major product (3 points).
CH3
H3C
CH3
H3C
CH3
___2-methyl-2-pentene__________________
H2SO4
CH3
OH
180 oC
CH3
H3C
CH3
____4-methyl-2-pentene____________________
Explain:__2-methyl-2-pentene is major because more carbons attached to C=C bond carbons___
______________________________________________________________________________
____________________________________________________________________________
15. (3 points) Which reaction requires platinum as a catalyst?
a. oxidation of an aldehyde or ketone
b. reduction of an aldehyde or ketone
c. reaction of an aldehyde or ketone with an alcohol
d. All of the responses are reactions that are catalyzed by platinum.
ANS: B
PTS:
3