UP Academic League of Chemical Engineering Students (UP ALCHEMES)

Academics Affairs Committee Review and Tutorials Program, AY 2012-2013

Chem 31 First Exam (SAMPLE EXAM)
SOURCES: Chem 31 Sample Exams (dated 15 January 2005, 29 July 2006, 2 May 2007, and 23 July 2007)
I. MULTIPLE CHOICE: Write the letter of the best answer beside the number of the item.

1. An acidic isomer of C4H6.

A.

B.

C.

D.

For items 2-5, consider the structure of vitamin C:

O
H H HH O
C7
HO C1 C2 C3 C4
C
C5 6
H H H
OH
HO

2. Identify the hybridization of C5.

A. sp
B. sp2
C. sp3
D. p
3. How many C-C bonds are there in the structure of vitamin C?
A. 10
B. 6
C. 7
D. 8
4. What is the approximate bond angle of C3-C4-C5 bonds?
A. 120
B. 109.5
C. 180
5. Which is the most polar bond?
A. O-H
B. C-O
C. C-C
D. C=C

D. 250

OH

A.

OH
6. Which is the most acidic?
B. CH3OH
C.

D. all of these

7. Which of the following statements regarding alkanes are TRUE?

I. They react with oxygen producing carbon dioxide and water.
II. They undergo free radical halogenation in the absence of light.
III. They are insoluble with water but soluble in non-polar solvents such as toluene.
IV. They undergo nucleophilic substitution in the presence of UV light.
A. I and II
B. I and III
C. II and IV
D. III and IV
8. Cyclopropane is very unstable primarily due to:
A. steric strain
B. angle strain
C. torsional strain
D. none of
these
9. The staggered conformation of alkanes is more stable than eclipsed because of the absence of:
A. angle strain
B. steric strain
C. torsional strain
D. none of
these

10. The methyl groups of cis-1,2-dimethylcyclohexane in the chair form will have a configuration of:
A. equatorial, equatorial
B. axial, equatorial
C. A & B
D. none of these
11. What alkene will yield CHO-CHO, CH2O, and OHCCH2CH3 upon ozonolysis followed by Zn, H2O,
H+?
A. CH2=CHCH2CH2CH=CH2
B. CH3CH=CHCH=CHCH3
C. CH2=CHCH=CHCH2CH3
D. CH2=CHCH=CHCH=CH2
12. What is the product formed when (CH3)2CHCH=CH2 undergoes acid-catalyzed hydration?
A. (CH3)2CHCH2CH2OH
B. CH3CH2CCH3OHCH3
C. (CH3)2CHCHOHCH3
D. all of these
13. What is the product formed when CH3CCH undergoes catalytic hydration?
A. CH3COCH3
B. CH3CHOHCH3
C. CH3CH2CH=O
D. CH3CH2CH3
14. How many mono-brominated products will 2,4-dimethylpentane give upon reaction with Br 2 under
UV light?
A. 1
B. 2
C. 3
D. 4
15. The pi electrons of an alkene act as the _____ in an electrophilic addition reaction.
A. electrophile
B. free radical
C. nucleophile
D. none of
these
16. Which of the following reactions of 2-butene will NOT follow Markovnikovs rule?
A. Reaction with H2O, H2SO4
B. Reaction with BH3, then with OH-, H2O2, H2O
C. Reaction with HCl
D. All will follow Markovnikovs rule
17. 2-butyne + _______ cis-2-butene
A. H2, Lindlars catalyst
B. H2, Pt
C. Na in liquid NH3 D. none of these
18. What is the product of the reaction of 1-methylcyclohexene and HBr?
A. 1-bromo-2-methylcyclohexane
B. 3-bromo-1-methylcyclohexene
C. 1-bromo-1-methylcyclohexane
D. 6-bromo-1-methylcyclohexene
19. Which of the following is a chain termination step?
A. A + B AB
B. A + B A + B C. A 2 A
D. none of these

20. Which of the following is the most stable alkene?

A.

B.

C.

21. The intermolecular force involved in liquid butane is:

A. Covalent bonding B. H-bonding
C. Van der Waals
D. Dipole-dipole
22. The eclipsed conformation of n-butane at C2-C3 below is unstable due to:
H
CH3

A. Torsional and steric strain

C. Angular and steric strain

B. Steric strain only

D. Torsional and angular strain

23. In the more stable conformation of the cycloalkane below, the number of methyl groups in the
axial position is:
H3C
CH3

CH3

A. 3

B. 2

C. 1

D. 0

CH
CH3
24. Which of the following compounds would be the most stable free radical?

CH2

CH3
A.

CH3 H

H3C
H

CH3

B.

H3C

C.

CH3
25. The order of decreasing stability for the following

alkenes below is:

A
A. A>B>C

B
B. B>A>C

C. C>B>A

C
D. B>C>A

II. Draw at the back of this page what is described by each item.
1. The C5H12 isomer with the lowest boiling point.
2. The most stable C6H12 alkene.
3. The Haworth projection of cis-1,4-dimethylcyclohexane.
4. The most stable conformation of cis-1,4-dimethylcyclohexane.
5. Possible termination step in the free radical chlorination of CH 4.
III. Provide the missing starting material, reagents, intermediate, or product in each of the following
reactions.
B r2
h

(intermediate)

(Major product)

5
H 2O H
H 2O

N aO H , H 2O

B 2H

(intermediate)

(Major product)

H I

1) O

2 ) (C H 3)2S

8+9

21
C

C
H

22

CH
B 2H

H 2O
H

18

19 + 20

(intermediate)

(products)

15

H 2O

N aO H , H 2O

16

CH
ex cess H B r

17

14

1) O

2) Z n

N H

10

12

11

1) O

2 ) H 2O

13