EBK GET READY FOR ORGANIC CHEMISTRY
2nd Edition
ISBN: 9780321787989
Author: KARTY
Publisher: PEARSON CO
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Question
Chapter 10, Problem 10.68P
Interpretation Introduction
Interpretation:
It is to be explained why the E2 mechanism does not occur readily under the given condition.
Concept introduction:
Epoxide is a three membered ring involving an oxygen and two carbon atoms. The ring is highly strained. The small ring size forces the groups on the adjacent atoms to be 1200 away, that is, the dihedral angle between the oxygen atom and the hydrogen atom of the adjacent carbon is 1200. For the E2 elimination reactions to occur, the leaving groups and hydrogen atom of the adjacent carbon atom must be anticoplanar, which means the dihedral angle between them must be 1800. Due to this,
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This reaction is an example of conjugate addition of a nucleophile to an a,ß-unsaturated carbonyl.
LOCH3
H20
H3C
H3C°
OCH3
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Draw the two resonance structures of the enolate anion intermediate for this reaction.
Draw Zaitsev and Hofmann products that are expected when each of the following compounds
is treated with a strong base to give an E2 ELIMINATION product.
Hint: Some compounds cannot produce both elimination products because they do not have two
beta-hydrogen atoms: in these cases only ONE product will be possible. In cases when neither
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?
O A
O
O
O
B
U
Br
t
Zaitsev
Hofmann
only ONE product is possible
B
only ONE product is possible
Hofmann
Zaitsev
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Chapter 10 Solutions
EBK GET READY FOR ORGANIC CHEMISTRY
Ch. 10 - Prob. 10.1PCh. 10 - Prob. 10.2PCh. 10 - Prob. 10.3PCh. 10 - Prob. 10.4PCh. 10 - Prob. 10.5PCh. 10 - Prob. 10.6PCh. 10 - Prob. 10.7PCh. 10 - Prob. 10.8PCh. 10 - Prob. 10.9PCh. 10 - Prob. 10.10P
Ch. 10 - Prob. 10.11PCh. 10 - Prob. 10.12PCh. 10 - Prob. 10.13PCh. 10 - Prob. 10.14PCh. 10 - Prob. 10.15PCh. 10 - Prob. 10.16PCh. 10 - Prob. 10.17PCh. 10 - Prob. 10.18PCh. 10 - Prob. 10.19PCh. 10 - Prob. 10.20PCh. 10 - Prob. 10.21PCh. 10 - Prob. 10.22PCh. 10 - Prob. 10.23PCh. 10 - Prob. 10.24PCh. 10 - Prob. 10.25PCh. 10 - Prob. 10.26PCh. 10 - Prob. 10.27PCh. 10 - Prob. 10.28PCh. 10 - Prob. 10.29PCh. 10 - Prob. 10.30PCh. 10 - Prob. 10.31PCh. 10 - Prob. 10.32PCh. 10 - Prob. 10.33PCh. 10 - Prob. 10.34PCh. 10 - Prob. 10.35PCh. 10 - Prob. 10.36PCh. 10 - Prob. 10.37PCh. 10 - Prob. 10.38PCh. 10 - Prob. 10.39PCh. 10 - Prob. 10.40PCh. 10 - Prob. 10.41PCh. 10 - Prob. 10.42PCh. 10 - Prob. 10.43PCh. 10 - Prob. 10.44PCh. 10 - Prob. 10.45PCh. 10 - Prob. 10.46PCh. 10 - Prob. 10.47PCh. 10 - Prob. 10.48PCh. 10 - Prob. 10.49PCh. 10 - Prob. 10.50PCh. 10 - Prob. 10.51PCh. 10 - Prob. 10.52PCh. 10 - Prob. 10.53PCh. 10 - Prob. 10.54PCh. 10 - Prob. 10.55PCh. 10 - Prob. 10.56PCh. 10 - Prob. 10.57PCh. 10 - Prob. 10.58PCh. 10 - Prob. 10.59PCh. 10 - Prob. 10.60PCh. 10 - Prob. 10.61PCh. 10 - Prob. 10.62PCh. 10 - Prob. 10.63PCh. 10 - Prob. 10.64PCh. 10 - Prob. 10.65PCh. 10 - Prob. 10.66PCh. 10 - Prob. 10.67PCh. 10 - Prob. 10.68PCh. 10 - Prob. 10.69PCh. 10 - Prob. 10.70PCh. 10 - Prob. 10.71PCh. 10 - Prob. 10.72PCh. 10 - Prob. 10.73PCh. 10 - Prob. 10.74PCh. 10 - Prob. 10.1YTCh. 10 - Prob. 10.2YTCh. 10 - Prob. 10.3YTCh. 10 - Prob. 10.4YTCh. 10 - Prob. 10.5YTCh. 10 - Prob. 10.6YTCh. 10 - Prob. 10.7YTCh. 10 - Prob. 10.8YTCh. 10 - Prob. 10.9YTCh. 10 - Prob. 10.10YTCh. 10 - Prob. 10.11YTCh. 10 - Prob. 10.12YTCh. 10 - Prob. 10.13YTCh. 10 - Prob. 10.14YTCh. 10 - Prob. 10.15YTCh. 10 - Prob. 10.16YTCh. 10 - Prob. 10.17YTCh. 10 - Prob. 10.18YTCh. 10 - Prob. 10.19YT
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