Examine the synthesis problem which converts 3-methylbutanoic acid to 2- bromo-1-chloro-3-methylbutane. Which of the following reaction sequences will yield the correct product?

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter16: Aldehydes And Ketones
Section: Chapter Questions
Problem 16.63P
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Examine the synthesis problem which converts 3-methylbutanoic acid to 2-
bromo-1-chloro-3-methylbutane. Which of the following reaction sequences
will yield the correct product?
Br
O 1. LIAIH, in dry ether followed by the addition of H,O
2. Br2 + PBr3 followed by H2O
3. PCI3 in ether
O 1. PCI3 in ether
2. Br2 + PBr3 followed by H2O
3. LIAIH4 in dry ether followed by the addition of H20
O 1. Br2 + PBR3 followed by H,O
2. LIAIH, in dry ether followed by the addition of H20
3. PCI3 in ether
O 1. Br2 + PBR3 followed by H20
2. PCI3 in ether
3. LIAIH, in dry ether followed by the addition of H20
Transcribed Image Text:Examine the synthesis problem which converts 3-methylbutanoic acid to 2- bromo-1-chloro-3-methylbutane. Which of the following reaction sequences will yield the correct product? Br O 1. LIAIH, in dry ether followed by the addition of H,O 2. Br2 + PBr3 followed by H2O 3. PCI3 in ether O 1. PCI3 in ether 2. Br2 + PBr3 followed by H2O 3. LIAIH4 in dry ether followed by the addition of H20 O 1. Br2 + PBR3 followed by H,O 2. LIAIH, in dry ether followed by the addition of H20 3. PCI3 in ether O 1. Br2 + PBR3 followed by H20 2. PCI3 in ether 3. LIAIH, in dry ether followed by the addition of H20
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