Which of the following is expected to give a meso compound upon reduction with NaBH4 in methanol? COOH CHO A) B) H -OH H OH H -OH HO- -H CH2OH H- OH CH₂OH 0 A B D) CHO OHC OCH 3 H- OH H- -OH H3CO CHO H- -OH CH3

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter22: Carbonyl Alpha-substitution Reactions
Section22.SE: Something Extra
Problem 32MP: Treatment of a cyclic ketone with diazomethane is a method for accomplishing a ring-expansion...
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Which of the following is expected to give a meso
compound upon reduction with NaBH4 in methanol?
COOH
CHO
A)
B)
H
-OH
H
OH
H -OH
HO-
-H
CH2OH
H-
OH
CH₂OH
0
A
B
CHO
H-
OH
H-
-OH
H-
-OH
CH3
D)
OHC
OCH3
H3CO CHO
Transcribed Image Text:Which of the following is expected to give a meso compound upon reduction with NaBH4 in methanol? COOH CHO A) B) H -OH H OH H -OH HO- -H CH2OH H- OH CH₂OH 0 A B CHO H- OH H- -OH H- -OH CH3 D) OHC OCH3 H3CO CHO
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