Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Question
Chapter 16.8, Problem 32P
(a)
Interpretation Introduction
Interpretation:
The mechanisms for the following reactions should be determined.
- 1. The acid-base catalyzed hydrolysis of an imine to a carbonyl compound and a primary
amine . - 2. The acid-base catalyzed hydrolysis of an enamine to a carbonyl compounds and a secondary amine.
Concept introduction:
The chemical compound containing carbon and nitrogen double bond is known as imine.
Enamine is derived by the condensation of an
(b)
Interpretation Introduction
Interpretation:
The reason for the difference in mechanism of two reactions should be given.
Concept introduction:
The chemical compound containing carbon and nitrogen double bond is known as imine.
Enamine is derived by the condensation of an aldehyde and ketone with secondary amine.
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Write the mechanism for the following reactions:1. the acid-catalyzed hydrolysis of an imine to a carbonyl compound and a primary amine2. the acid-catalyzed hydrolysis of an enamine to a carbonyl compound and a secondary amine
6. The reaction between aniline and nitrous
acid at low temperature yields
A) an N-nitroso amine
B) a diazonium salt
C) a nitrile
D) an amine nitrite salt
7. An organic nitrogen compound, X, gives
ammonia on warming with dilute aqueous
sodium hydroxide, X could be
A) ethanamide B) ethylamine
C) phenylamine D) amino ethanoic acid
1. Which of the following amines would make an imine if reacted with an aldehyde or ketone?
A
B
e. Which of the following moleculo
C
NH₂
AN
D
Chapter 16 Solutions
Organic Chemistry (8th Edition)
Ch. 16.1 - Give two names for each of the following:Ch. 16.1 - Prob. 2PCh. 16.1 - Name the following:Ch. 16.2 - Prob. 4PCh. 16.4 - What products are formed when the following...Ch. 16.4 - We saw on the previous page that...Ch. 16.4 - a. How many stereoisomers are obtained from the...Ch. 16.4 - Prob. 9PCh. 16.4 - Write the mechanism for the reaction of acetyl...Ch. 16.4 - Prob. 11P
Ch. 16.4 - Show how the following compounds can be...Ch. 16.4 - Prob. 13PCh. 16.4 - Prob. 14PCh. 16.4 - In the mechanism for cyanohydrin formation, why is...Ch. 16.4 - Prob. 16PCh. 16.4 - Prob. 17PCh. 16.4 - Show two ways to convert an alkyl halide into a...Ch. 16.5 - Prob. 20PCh. 16.5 - Prob. 21PCh. 16.5 - Prob. 22PCh. 16.5 - Prob. 23PCh. 16.6 - Prob. 24PCh. 16.7 - What reducing agents should be used to obtain the...Ch. 16.7 - Prob. 26PCh. 16.8 - Prob. 27PCh. 16.8 - Prob. 28PCh. 16.8 - Prob. 29PCh. 16.8 - The pKa of protonated acetone is about 7.5. and...Ch. 16.8 - Prob. 31PCh. 16.8 - Prob. 32PCh. 16.8 - Prob. 33PCh. 16.8 - Excess ammonia must be used when a primary amine...Ch. 16.8 - The compounds commonly known as amino acids are...Ch. 16.9 - Hydration of an aldehyde is also catalyzed by...Ch. 16.9 - Which ketone forms the most hydrate in an aqueous...Ch. 16.9 - When trichloroacetaldehyde is dissolved in water,...Ch. 16.9 - Which of the following are a. hermiacetals? b....Ch. 16.9 - Prob. 40PCh. 16.9 - Explain why an acetal can be isolated but most...Ch. 16.10 - Prob. 42PCh. 16.10 - Prob. 43PCh. 16.10 - What products would be formed from the proceedings...Ch. 16.10 - a. In a six-step synthesis, what is the yield of...Ch. 16.10 - Show how each of the following compounds could be...Ch. 16.12 - Prob. 47PCh. 16.13 - Prob. 49PCh. 16.14 - Prob. 50PCh. 16.15 - Prob. 51PCh. 16.16 - Prob. 52PCh. 16 - Draw the structure for each of the following: a....Ch. 16 - Prob. 54PCh. 16 - Prob. 55PCh. 16 - Prob. 56PCh. 16 - a. Show the reagents required to form the primary...Ch. 16 - Prob. 58PCh. 16 - Prob. 59PCh. 16 - Using cyclohexanone as the starting material,...Ch. 16 - Propose a mechanism for each of the following...Ch. 16 - Show how each of the following compounds can be...Ch. 16 - Fill in the boxes:Ch. 16 - Prob. 64PCh. 16 - Identify A through O:Ch. 16 - Prob. 66PCh. 16 - Prob. 67PCh. 16 - Prob. 68PCh. 16 - How many signals would the product of the...Ch. 16 - Prob. 70PCh. 16 - Prob. 71PCh. 16 - Prob. 72PCh. 16 - Prob. 73PCh. 16 - Prob. 74PCh. 16 - Prob. 75PCh. 16 - Prob. 76PCh. 16 - Prob. 77PCh. 16 - Prob. 78PCh. 16 - Draw structure for A-D for each of the following:Ch. 16 - Prob. 80PCh. 16 - a. Propose a mechanism for the following reaction:...Ch. 16 - Prob. 82PCh. 16 - A compound gives the following IR spectrum. Upon...Ch. 16 - How can be following compounds be prepared from...Ch. 16 - Prob. 85PCh. 16 - Prob. 86PCh. 16 - Prob. 87PCh. 16 - In the presence of an acid catalyst, acetaldehyde...Ch. 16 - Prob. 89PCh. 16 - Prob. 90PCh. 16 - Prob. 91PCh. 16 - A compound reacts with methylmagnesium bromide...Ch. 16 - Show how each of the following compounds can be...Ch. 16 - Prob. 94PCh. 16 - The pKa values of the carboxylic acid groups of...Ch. 16 - The Baylis-Hillman reaction is a DABCO...Ch. 16 - Prob. 97PCh. 16 - Prob. 98P
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- Chapter 1 (Carbonyl compounds I) Explain how the class I carbonyl compound reacts? What will be the product when ethylamine and propyl amine reacts with acetyl chloride? Why only one amide obtained after the reaction of acetyl chloride with a mixture of ethylamine and trimethylamine? Excess amine is required in the reaction of acetyl chloride with amine whereas excess alcohol is not required in the reaction of acetyl chloride and alcohol. Why? List the following ester in order of decreasing reactivities towards hydrolysis with reason: Methyl benzoate, p-nitro methyl benzoate and p-methoxy methyl benzoate The reaction of an ester with an amine is not as slow as the reaction of an ester with water or an alcohol. Explain with reason. Explain why the rate of aminolysis of an ester cannot be increased by H+, OH- or OR-. How can you activate the carboxylic acid? Is acid catalyzed hydrolysis of acetamide a reversible or an irreversible reaction. Explain. Chapter 2 (Carbonyl compounds II)…arrow_forwardSee image belowarrow_forwardWhat alkyl halide is needed to prepare each 1° amine by the Gabriel synthesis?arrow_forward
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