Organic Chemistry

Problems 477

39. Indicate which alcohol will undergo dehydration more rapidly when heated with

a. d.

b. e.

c. f.

40. Which of the following alkyl halides could be successfully used to form a Grignard reagent?

a. b. c. d.

41. Starting with (R)-1-deuterio-1-propanol, how could you prepare:
    a. (S)-1-deuterio-1-propanol? b. (S)-1-deuterio-1-methoxypropane? c. (R)-1-deuterio-1-methoxypropane?


42. What alkenes would you expect to be obtained from the acid-catalyzed dehydration of 1-hexanol?


43. Give the product of each of the following reactions:

a.

d. g.

b. e. h.

c. f.

44. When heated with both 3,3-dimethyl-2-butanol and 2,3-dimethyl-2-butanol are dehydrated to form 2,3-dimethyl-2-butene.
    Which alcohol dehydrates more rapidly?


45. Using the given starting material, any necessary inorganic reagents, and any carbon-containing compounds with no more than two
    carbon atoms, indicate how the following syntheses could be carried out:

a. d.

b. e.

c. f. CH 3 CHCH 2 OH

CH 3

CH 3 CHCH 2 CH 2 CH 2 OH

CH 3

Br CH 2 CH 2 OH

CH 3 CH 2 C CH CH 3 CH 2 C CCH 2 CH 2 OH

O

CH 3

OH Cl CH 2 CH 2 CN

H 2 SO 4 ,

O

CH 3 OH

H 2 SO (^4) CH 3 O−
CH 3 CH 2 CHCCH (^3) ∆
OH CH 3
CH 3
(CH 3 CH 2 CH 2 ) 2 CuLi
Cl
O
H+
CH 3 OH
∆
CH 3 CHCH 2 OCH 3 + HI
CH 3
H
OH
H
CH 3

2. NaC N


3. TsCl/pyridine
   CH 3 CH CCH 3

OH

CH 3

∆

H 2 SO 4

CH 3

∆

CH 3 COCH 2 CH 3 + HBr

CH 3

CH 3

CH 3 NCH 2 CH 2 CH 2 Br H 2 NCH 2 CH 2 CH 2 Br

CH 3

BrCH 2 CH 2 CH 2 COH

O

HOCH 2 CH 2 CH 2 CH 2 Br

CH 3 CH 2 CHCH 3 or

OH

CH 3 CCH 2 CH 3

OH

CH 3

or

OH CH 3

OH

H 3 C

or

CH 2 CH 2 OH

OH

CHCH 3

or

OH OH

OH

or

CHCH 3

OH

CHCH 3

or

CH 2 OH CH 2 CH 2 OH

H 2 SO 4.

BRUI12-437_480r3 27-03-2003 11:51 AM Page 477