ONa (a) -Br ONa (b) (c) Br NaOH ÓH (d) OOH (e) NaN3 dioxane-water Br NH3 (f) methanol (g) CH,ONa CH3OH" HCI (h) CHCI3 1. LIAIH4, diethyl ether (i) 2. H-О (j) CH3(CH,)16CH,OTs + CH;CHCH,CH,SNa -CH3 C,H;SNa H- (k) CI H-

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter22: Carbonyl Alpha-substitution Reactions
Section22.SE: Something Extra
Problem 63AP: As far back as the 16th century, South American Incas chewed the leaves of the coca bush,...
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Predict the principal organic product of each of the following reactions. Specify stereochemistry where appropriate.

ONa
(a)
-Br
ONa
(b)
(c)
Br
NaOH
ÓH
(d)
OOH
(e)
NaN3
dioxane-water
Br
NH3
(f)
methanol
Transcribed Image Text:ONa (a) -Br ONa (b) (c) Br NaOH ÓH (d) OOH (e) NaN3 dioxane-water Br NH3 (f) methanol
(g)
CH,ONa
CH3OH"
HCI
(h)
CHCI3
1. LIAIH4, diethyl ether
(i)
2. H-О
(j) CH3(CH,)16CH,OTs + CH;CHCH,CH,SNa
-CH3 C,H;SNa
H-
(k)
CI
H-
Transcribed Image Text:(g) CH,ONa CH3OH" HCI (h) CHCI3 1. LIAIH4, diethyl ether (i) 2. H-О (j) CH3(CH,)16CH,OTs + CH;CHCH,CH,SNa -CH3 C,H;SNa H- (k) CI H-
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