Chemistry 331 - Fall 1996

Quiz, Chapter 8 - Answer Key

Use the following letter codes to represent the reagents indicated below:

A - NaBH4
B - LiAlH4
C - KMnO4
D - CrO3
E - PCC (pyridinium chlorochromate)
F - RCO3H
G - H2SO4
H - HBr
I - HI
J - PBr3
K - SOCl2
L - KOH
M - NaSH
N - Na


1. (1/2 point each) Give a correct and complete name for the major product expected from the following reactions:

1. 1-butanol + J ---> 1-bromobutane (or n-butyl bromide)

2. (R)-2-butanol + N ---> sodium (R)-2-butoxide

3. tert-butyl alcohol + H ---> tert-butyl bromide (or 2-bromo-2-methylpropane)

4. acetone + A ---> 2-propanol (or isopropyl alcohol)

5. trans-2-pentene + F ---> trans-2-ethyl-3-methyloxirane (racemic)

6. methyl phenyl ether + I ---> phenol + methyl iodide (or iodomethane)

7. p-methoxyphenol + L ---> potassium p-methoxyphenoxide

8. product from reaction 1 + M ---> 1-butanethiol (or n-butyl mercaptan)

9. benzyl alcohol + D ---> benzoic acid

10. acetic acid + B ---> ethanol (or ethyl alcohol)


2. (1/2 point each) Indicate how each of the reactions above would be classified (use reaction numbers):

a) oxidations: 5, 9

b) reductions: 4, 10 (2 also acceptable here)

c) substitutions: 1, 3, 6, 8

d) acid/base reactions: 2, 7


3. (1 point each) Four of the lettered reagents were not used in the reactions above. Explain the type of reaction each would be useful for and give a specific example:

(example: C - KMnO4 is a strong oxidant,

e.g., it would oxidize toluene to benzoic acid)

E - a selective oxidant, used to convert 1° alcohols to aldehydes

G - a strong acid, may be used to dehydrate alcohols

K - a chlorinating agent, used to convert 1° or 2° alcohols to chlorides