Answered: OPP 11 OPP 11 + farnesyl pyrophosphate…

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OPP 11 OPP 11 + farnesyl pyrophosphate nerolidyl pyrophosphate 1 I epi-cedrol OH 3 Ι + 2 +

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:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Chapter22: Proteins

Section: Chapter Questions

Problem 22.77P

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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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F NO2 + NaOCH2CH3