Introduction to General, Organic and Biochemistry
Introduction to General, Organic and Biochemistry
11th Edition
ISBN: 9781285869759
Author: Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher: Cengage Learning
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Question

A. Provide a stepwise mechanism for the formation of nerolidyl pyrophosphate from
farnesylpyrophosphate 
B. Provide a stepwise mechanism for the formation of carbocation 1 from nerolidyl
pyrophosphate. Number the backbone carbons of nerolidyl pyrophosphate from 1 to 11 as shown, and
include the carbon numbering in your structure of 1 
C. Following from B, give an arrow-pushing mechanism to convert 1 to 2 and 2 to 3. Use the
backbone carbon numbering from 1 to indicate where carbon atoms ended up in 2 and 3 
D. In addition to forming epi-cedrol, carbocation 3 gives three minor byproducts: a diastereomeric
alcohol and two alkenes. Draw mechanisms that could give rise to these three products

OPP 11 OPP 11 + farnesyl pyrophosphate nerolidyl pyrophosphate 1 I epi-cedrol OH 3 Ι + 2 +
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Transcribed Image Text:OPP 11 OPP 11 + farnesyl pyrophosphate nerolidyl pyrophosphate 1 I epi-cedrol OH 3 Ι + 2 +
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