Organic Chemistry

Problems 875

9. Oxidation of hydroquinones and reduction of quinones (Section 20.12).

O

O

OH

OH

(KSO 3 ) 2 NO

NaBH 4

reduction

oxidation

Key Terms

Baeyer–Villiger oxidation (p. 853)

catalytic hydrogenation (p. 844)

chemoselective reaction (p. 848)

dissolving-metal reduction (p. 846)

enantioselective reaction (p. 857)

epoxidation (p. 855)

functional group interconversion (p. 867)

glycol (p. 858)

metal-hydride reduction (p. 846)

molozonide (p. 862)

oxidation (p. 842)

oxidation–reduction reaction (p. 841)

oxidation state (p. 842)

oxidative cleavage (p. 860)

oxidizing agent (p. 841)

ozonide (p. 862)

ozonolysis (p. 861)

peroxyacid (p. 853)

redox reaction (p. 841)

reducing agent (p. 841)

reduction (p. 842)

Rosenmund reduction (p. 845)

Swern oxidation (p. 851)

Tollens test (p. 853)

vicinal diol (p. 858)

vicinal glycol (p. 858)

Problems

34. Fill in the blank with “oxidized”or “reduced.”
    a. Secondary alcohols are to ketones.
    b. Acyl halides are to aldehydes.
    c. Aldehydes are to primary alcohols.
    d. Alkenes are to aldehydes and/or ketones.
    e. Aldehydes are to carboxylic acids.
    f. Alkenes are to 1,2-diols.
    g. Alkenes are _____ to alkanes.


35. Give the products of the following reactions. Indicate whether each reaction is an oxidation or a reduction:

a. f.

b. g.

c. h.

d. i.

e. j. CH

O

H 2

CH 3 CH 2 CH CHCH 2 CH (^3) Raney Ni

1. O 3 , – 78 °C


2. Zn, H 2 O

CC

H 3 CH

H CH 3

RCOOH

O

CH 3 CH 2 CCH

1. disiamylborane


2. H 2 O 2 , HO−, H 2 O


3. LiAlH 4


4. H 3 O+

COCHCH 3

O

CH 3

1. LiAlH 4


2. H 3 O+

H 2

partially

deactivated Pd

CH 3 CH 2 CH 2 CCl

O

CH

O

RCOOH

O

CH CH (^2) HO−, ∆
KMnO 4
CH 3 CH 2 CH 2 CNHCH 3

1. LiAlH 4


2. H 2 O

O

Na 2 Cr 2 O 7

CH 3 CH 2 CH 2 CH 2 CH 2 OH H 2 SO 4

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