Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Question
Chapter 19, Problem 19.31P
Interpretation Introduction
Interpretation:
The curved-arrow mechanism for the acid-catalyzed hydrolysis of the imine derivative from benzaldehyde and ethylamine is to be predicted.
Concept introduction:
The imine is a kind of organic compound which is formed by the reaction of a carbonyl compound with an
The imines can undergo hydrolysis reaction to form carbonyl compound and an amine.
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H
NH₂
ཡིནྣཾ ༥ ཨ ཨནྡྷ༥ ༠ ཨི་ཝཱ, ཙ ཨ་ར༩
H
NH3+
the acidity of the amine ion drives the reaction to shift toward the conjugate base of the carboxylic acid product.
the resulting carboxylic acid ion is a weaker base than an acetate ion.
O aldehydes are more reactive toward nucleophiles than ketones.
Onucleophilic attack occurs preferentially at the less hindered carbon of the formyl group.
(a) Draw the three isomers of benzenedicarboxylic acid.(b) The isomers have melting points of 210 °C, 343 °C, and 427 °C. Nitration of the isomers at all possible positions was once used to determine their structures. The isomer that melts at 210 °C gives two mononitro isomers. The isomer that melts at 343 °C gives three mononitro isomers. The isomer that melts at 427 °C gives only one mononitro isomer. Show which isomer has which melting point.
Give the chemical tests to distinguish between following pair of compounds :
(i) Propanol and propanone
(ii) Ethyl acetate and methyl acetate
(iii) Benzaldehyde and benzoic acid
(iv) Benzaldehyde and acetaldehyde
(v) Formic acid and acetic acid
(vi) Propanal and propanol
(vii) Ethanoic acid and ethylethanoate
Chapter 19 Solutions
Organic Chemistry
Ch. 19 - Prob. 19.1PCh. 19 - Prob. 19.2PCh. 19 - Prob. 19.3PCh. 19 - Prob. 19.4PCh. 19 - Prob. 19.5PCh. 19 - Prob. 19.6PCh. 19 - Prob. 19.7PCh. 19 - Prob. 19.8PCh. 19 - Prob. 19.9PCh. 19 - Prob. 19.10P
Ch. 19 - Prob. 19.11PCh. 19 - Prob. 19.12PCh. 19 - Prob. 19.13PCh. 19 - Prob. 19.14PCh. 19 - Prob. 19.15PCh. 19 - Prob. 19.16PCh. 19 - Prob. 19.17PCh. 19 - Prob. 19.18PCh. 19 - Prob. 19.19PCh. 19 - Prob. 19.20PCh. 19 - Prob. 19.21PCh. 19 - Prob. 19.22PCh. 19 - Prob. 19.23PCh. 19 - Prob. 19.24PCh. 19 - Prob. 19.25PCh. 19 - Prob. 19.26PCh. 19 - Prob. 19.27PCh. 19 - Prob. 19.28PCh. 19 - Prob. 19.29PCh. 19 - Prob. 19.30PCh. 19 - Prob. 19.31PCh. 19 - Prob. 19.32PCh. 19 - Prob. 19.33PCh. 19 - Prob. 19.34PCh. 19 - Prob. 19.35PCh. 19 - Prob. 19.36PCh. 19 - Prob. 19.37PCh. 19 - Prob. 19.38PCh. 19 - Prob. 19.39PCh. 19 - Prob. 19.40APCh. 19 - Prob. 19.41APCh. 19 - Prob. 19.42APCh. 19 - Prob. 19.43APCh. 19 - Prob. 19.44APCh. 19 - Prob. 19.45APCh. 19 - Prob. 19.46APCh. 19 - Prob. 19.47APCh. 19 - Prob. 19.48APCh. 19 - Prob. 19.49APCh. 19 - Prob. 19.50APCh. 19 - Prob. 19.51APCh. 19 - Prob. 19.53APCh. 19 - Prob. 19.54APCh. 19 - Prob. 19.55APCh. 19 - Prob. 19.56APCh. 19 - Prob. 19.57APCh. 19 - Prob. 19.58APCh. 19 - Prob. 19.59APCh. 19 - Prob. 19.60APCh. 19 - Prob. 19.61APCh. 19 - Prob. 19.62APCh. 19 - Prob. 19.63APCh. 19 - Prob. 19.64APCh. 19 - Prob. 19.65APCh. 19 - Prob. 19.66APCh. 19 - Prob. 19.67APCh. 19 - Prob. 19.68APCh. 19 - Prob. 19.69APCh. 19 - Prob. 19.70APCh. 19 - Prob. 19.71APCh. 19 - Prob. 19.72AP
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