EBK ORGANIC CHEMISTRY
7th Edition
ISBN: 9780133556186
Author: Bruice
Publisher: VST
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Chapter 25, Problem 67P
Propose a mechanism for the biosynthesis of α-pinene from farnesyl pyrophosphate.
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13. (11pts total) Consider the arrows pointing at three different carbon-carbon bonds in the
molecule depicted below.
Bond B
2°C. +2°C. cleavage
Bond A
•CH3 + 26.← Cleavage
2°C. +
Bond C
+3°C•
CH3 2C
Cleavage
E
2°C. 26.
weakest bond
Intact molecule
Strongest 3°C 20.
Gund
Largest
argest
a. (2pts) Which bond between A-C is weakest? Which is strongest? Place answers in
appropriate boxes.
C
Weakest
bond
A
Produces
Most
Bond
Strongest
Bond
Strongest Gund
produces least stable
radicals
Weakest
Stable radical
b. (4pts) Consider the relative stability of all cleavage products that form when bonds A,
B, AND C are homolytically cleaved/broken. Hint: cleavage products of bonds A, B,
and C are all carbon radicals.
i. Which ONE cleavage product is the most stable? A condensed or bond line
representation is fine.
13°C. formed in
bound C
cleavage
ii. Which ONE cleavage product is the least stable? A condensed or bond line
representation is fine.
• CH3
methyl radical
Formed in Gund A Cleavage
c.…
Br.
COOH Br,
FCH COOH E
FeBr
ASOCI
B
NH
(CH,CO),OD Br₂
2
C
alcKOH
Find A to F (all)
Chapter 25 Solutions
EBK ORGANIC CHEMISTRY
Ch. 25.6 - Prob. 2PCh. 25.6 - Prob. 3PCh. 25.6 - Why does the OH group add to the -carbon rather...Ch. 25.6 - Prob. 5PCh. 25.6 - How many molecules of NADH are formed from the...Ch. 25.7 - Prob. 7PCh. 25.7 - Prob. 8PCh. 25.7 - The oxidation of glyceraldehyde-3-phosphate to...Ch. 25.7 - Prob. 10PCh. 25.8 - Prob. 11P
Ch. 25.8 - Prob. 12PCh. 25.8 - Prob. 13PCh. 25.8 - Propose a mechanism for the reduction of...Ch. 25.9 - Prob. 15PCh. 25.9 - Prob. 16PCh. 25.10 - Acid-catalyzed dehydration reactions are normally...Ch. 25.10 - Prob. 18PCh. 25.10 - Prob. 19PCh. 25.10 - Acid-catalyzed dehydration reactions are normally...Ch. 25.10 - Prob. 21PCh. 25.10 - Prob. 22PCh. 25.11 - Prob. 23PCh. 25.12 - a. What is the name of the enzyme that converts...Ch. 25.15 - Prob. 25PCh. 25.16 - Prob. 26PCh. 25.16 - Prob. 27PCh. 25.17 - Propose mechanisms for the Claisen condensation...Ch. 25.17 - Prob. 29PCh. 25.17 - Propose a mechanism for the conversion of...Ch. 25.17 - Propose a mechanism for the biosynthesis of...Ch. 25.17 - Propose a mechanism for the conversion of the E...Ch. 25.17 - The fluoro-substitued geranyl pyrophosphate shown...Ch. 25.17 - Prob. 35PCh. 25.18 - Draw the individual 1,2-hydride and 1,2-methyl...Ch. 25 - Prob. 38PCh. 25 - Prob. 39PCh. 25 - Prob. 40PCh. 25 - Prob. 41PCh. 25 - Prob. 42PCh. 25 - Prob. 43PCh. 25 - Prob. 44PCh. 25 - Prob. 45PCh. 25 - Prob. 46PCh. 25 - Prob. 47PCh. 25 - Prob. 48PCh. 25 - Prob. 49PCh. 25 - Prob. 50PCh. 25 - Prob. 51PCh. 25 - Prob. 52PCh. 25 - Prob. 53PCh. 25 - Prob. 54PCh. 25 - Prob. 55PCh. 25 - Prob. 56PCh. 25 - Prob. 57PCh. 25 - Prob. 58PCh. 25 - Prob. 59PCh. 25 - Prob. 60PCh. 25 - Prob. 61PCh. 25 - Prob. 62PCh. 25 - UDP-galactose-4-epimerase converts UDP-galactose...Ch. 25 - A student is trying to determine the mechanism for...Ch. 25 - What would be the results of the experiment in...Ch. 25 - Prob. 66PCh. 25 - Propose a mechanism for the biosynthesis of...Ch. 25 - Eudesmol is a sesquiterpene found in eucalyptus....
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