What reaction sequence can be used to convert methyl 3-oxocyclopentane- 1-carboxylate to 3-(2-hydroxypropan- 2-yl)cyclopentan-1-one.

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter22: Carbonyl Alpha-substitution Reactions
Section22.SE: Something Extra
Problem 27MP
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What reaction sequence can be used to
convert methyl 3-oxocyclopentane-
1-carboxylate to 3-(2-hydroxypropan-
2-yl)cyclopentan-1-one.
a) 2 MeMgBr, em NH,*
b) HOCH¿CH2OH, H30*/ LIAIH4, éter/ 2 MeMgBr, em NH,*
c) HOCH2CH,OH, H3O*/ 2 MeMgBr, em NH,*
d) HOCH,CH2OH, H30*/ H2, Pt / 2 MeMgBr, em NH,*
e) none of these
Transcribed Image Text:What reaction sequence can be used to convert methyl 3-oxocyclopentane- 1-carboxylate to 3-(2-hydroxypropan- 2-yl)cyclopentan-1-one. a) 2 MeMgBr, em NH,* b) HOCH¿CH2OH, H30*/ LIAIH4, éter/ 2 MeMgBr, em NH,* c) HOCH2CH,OH, H3O*/ 2 MeMgBr, em NH,* d) HOCH,CH2OH, H30*/ H2, Pt / 2 MeMgBr, em NH,* e) none of these
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