B LOH A OH NaH PBr3 C D F (a) Name the functional groups in compounds A, B and F, including, if relevant, whether they are primary (1°), secondary (2°) or tertiary (3). (b) Propose a reagent that could be used to convert A into B. (c) Draw the structure of intermediate C formed by reaction of A with NaH.

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter22: Carbonyl Alpha-substitution Reactions
Section22.SE: Something Extra
Problem 64AP: The key step in a reported laboratory synthesis of sativene, a hydrocarbon isolated from the mold...
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Please answer parts a,b,c

B
OH
?
A
LOH
NaH
PBr3
C
D
?
F
(a) Name the functional groups in compounds A, B and F, including, if relevant, whether they
are primary (1°), secondary (2°) or tertiary (3°).
(b) Propose a reagent that could be used to convert A into B.
(c) Draw the structure of intermediate C formed by reaction of A with NaH.
(d) Draw the curly (curved) arrows for the conversion of A into C.
(e) Give a suitable reagent to convert C into F.
(f) Propose the structure of organic compound D formed by reaction with PBr3.
(g) Could HBr be used for the conversion of A into D? Explain very briefly.
Transcribed Image Text:B OH ? A LOH NaH PBr3 C D ? F (a) Name the functional groups in compounds A, B and F, including, if relevant, whether they are primary (1°), secondary (2°) or tertiary (3°). (b) Propose a reagent that could be used to convert A into B. (c) Draw the structure of intermediate C formed by reaction of A with NaH. (d) Draw the curly (curved) arrows for the conversion of A into C. (e) Give a suitable reagent to convert C into F. (f) Propose the structure of organic compound D formed by reaction with PBr3. (g) Could HBr be used for the conversion of A into D? Explain very briefly.
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