
Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)
2nd Edition
ISBN: 9780393655551
Author: KARTY, Joel
Publisher: W. W. Norton & Company
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Chapter D, Problem D.2P
Interpretation Introduction
Interpretation:
The orbital interaction that illustrates the most significant hyperconjugation interaction in
Concept introduction:
The HOMO is the highest occupied molecular orbital. If the HOMO and LUMO orbitals can interact, then the interaction stabilizes the entire species. The species that contribute to the pertinent HOMO in the interaction is relatively electron-rich. It is the Lewis base or the nucleophile. The species that contribute the pertinent LUMO is relatively electron-poor. It is the Lewis acid or the electrophile.
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Redraw the tripeptide with or without its acidic hydrogensto demonstrate where the total charge of -2 comes from: *see image
2. Consider the data below to answer the following questions.
Cyanohydrins are important intermediates in the synthesis of α-hydroxycarboxylic acids from ketones and
aldehydes. The nitrile functional group can be hydrolyzed by aqueous acid to yield a carboxylic acid.
Nitriles can also be hydrolyzed to carboxylic acids using aqueous base. Unfortunately, when a cyanohydrin
is treated with aqueous base the original carbonyl compound is isolated.
OH
CH-COOH
0
HO CN
C
H30*
C.
H
H
HC N
NaOH
H₂O
C=O
0
cyanohydrin
H
+ NaCN + H₂O
Chapter D Solutions
Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)
Ch. D - Prob. D.1PCh. D - Prob. D.2PCh. D - Prob. D.3PCh. D - Prob. D.4PCh. D - Prob. D.5PCh. D - Prob. D.6PCh. D - Prob. D.7PCh. D - Prob. D.8PCh. D - Prob. D.9PCh. D - Prob. D.10P
Ch. D - Prob. D.11PCh. D - Prob. D.1YTCh. D - Prob. D.2YTCh. D - Prob. D.3YTCh. D - Prob. D.4YTCh. D - Prob. D.5YTCh. D - Prob. D.6YTCh. D - Prob. D.7YTCh. D - Prob. D.8YTCh. D - Prob. D.9YTCh. D - Prob. D.10YTCh. D - Prob. D.11YTCh. D - Prob. D.12YTCh. D - Prob. D.13YTCh. D - Prob. D.14YTCh. D - Prob. D.15YTCh. D - Prob. D.16YT
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