Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Question
Chapter 21.SE, Problem 30VC
Interpretation Introduction
Interpretation:
To compare the amide (acetamide) and an acyl azide (acetyl azide) and identify which is more reactive in nucleophilic acyl substitution reactions.
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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
Amidation Reactions
Part A
Learning Goal:
To identify characteristics common to all amidation reactions, and to apply these generalities in drawing specific amidation reactants
or products.
Part B
Amidation reactions are condensation reactions. In a condensation reaction, two molecules join with a new covalent bond, and this
results from the removal of a small molecule such as a water molecule. The reactants in amidation are a carboxylic acid and an
amine, and the products are an amide and a water molecule. The carboxylic acid reactant can be of any type. The amine can be
simple ammonia (NH₂). a primary amine. or a secondary amine. It cannot be a tertiary amine because tertiary amines lack the N-H
Aspartame, an amide, is the sweetener commonly used in diet cola.
COOH
CH2
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33 of 38
Review | Constants | Periodic Table
CH2
O
H₂N CH C NH-CH-COOCH3
7
H 2D EXP. CONT.
aspartame
Draw the carboxylic acid that is a reactant in the production of aspartame.
Draw the molecule on the canvas by…
Chapter 21 Solutions
Organic Chemistry
Ch. 21.1 - Give IUPAC names for the following substances:Ch. 21.1 - Draw structures corresponding to the following...Ch. 21.2 - Prob. 3PCh. 21.2 - Rank the compounds in each of the following sets...Ch. 21.2 - Predict the products of the following nucleophilic...Ch. 21.2 - Prob. 6PCh. 21.3 - Prob. 7PCh. 21.3 - If the following molecule is treated with acid...Ch. 21.4 - How might you prepare the following esters using a...Ch. 21.4 - Prob. 10P
Ch. 21.4 - Prob. 11PCh. 21.4 - Prob. 12PCh. 21.4 - Prob. 13PCh. 21.5 - Prob. 14PCh. 21.5 - What product would you expect from reaction of one...Ch. 21.6 - Prob. 16PCh. 21.6 - Prob. 17PCh. 21.6 - Show the products you would obtain by reduction of...Ch. 21.6 - What ester and what Grignard reagent might you...Ch. 21.7 - Prob. 20PCh. 21.7 - How would you use the reaction of an amide with...Ch. 21.8 - Write the mechanism of the reaction shown in...Ch. 21.9 - Prob. 23PCh. 21.9 - Prob. 24PCh. 21.10 - Prob. 25PCh. 21.10 - Prob. 26PCh. 21.SE - Name the following compounds:Ch. 21.SE - Prob. 28VCCh. 21.SE - Prob. 29VCCh. 21.SE - Prob. 30VCCh. 21.SE - Predict the product(s) and provide the mechanism...Ch. 21.SE - Predict the product(s) and provide the mechanism...Ch. 21.SE - Predict the product(s) and provide the mechanism...Ch. 21.SE - Predict the product(s) and provide the complete...Ch. 21.SE - Prob. 35MPCh. 21.SE - When 4-dimethylaminopyridine (DMAP) is added in...Ch. 21.SE - Prob. 37MPCh. 21.SE - Prob. 38MPCh. 21.SE - Prob. 39MPCh. 21.SE - The hydrolysis of a biological thioester to the...Ch. 21.SE - Prob. 41MPCh. 21.SE - Prob. 42MPCh. 21.SE - Prob. 43MPCh. 21.SE - In the iodoform reaction, a triiodomethyl ketone...Ch. 21.SE - Give IUPAC names for the following compounds:Ch. 21.SE - Prob. 46APCh. 21.SE - Draw and name compounds that meet the following...Ch. 21.SE - Predict the product, if any, of reaction between...Ch. 21.SE - Prob. 49APCh. 21.SE - Prob. 50APCh. 21.SE - What product would you expect to obtain from...Ch. 21.SE - Prob. 52APCh. 21.SE - Prob. 53APCh. 21.SE - The following reactivity order has been found for...Ch. 21.SE - Prob. 55APCh. 21.SE - Outline methods for the preparation of...Ch. 21.SE - Prob. 57APCh. 21.SE - When ethyl benzoate is heated in methanol...Ch. 21.SE - tert-Butoxycarbonyl azide, a reagent used in...Ch. 21.SE - Prob. 60APCh. 21.SE - Prob. 61APCh. 21.SE - What is the structure of the polymer produced by...Ch. 21.SE - Polyimides with the structure shown are used as...Ch. 21.SE - Prob. 64APCh. 21.SE - Propose a structure for a compound, C4H7ClO2, that...Ch. 21.SE - Assign structures to compounds with the following...Ch. 21.SE - Prob. 67APCh. 21.SE - When a carboxylic acid is dissolved in...Ch. 21.SE - Prob. 69APCh. 21.SE - Prob. 70APCh. 21.SE - Prob. 71APCh. 21.SE - Phenyl 4-aminosalicylate is a drug used in the...Ch. 21.SE - N,N-Diethyl-m-toluamide (DEET) is the active...Ch. 21.SE - Tranexamic acid, a drug useful against blood...Ch. 21.SE - One frequently used method for preparing methyl...Ch. 21.SE - Prob. 76APCh. 21.SE - Assign structures to compounds with the following...Ch. 21.SE - Propose structures for compounds with the...Ch. 21.SE - Propose a structure for the compound with the...Ch. 21.SE - Draw the structure of the compound that produced...Ch. 21.SE - Prob. 81APCh. 21.SE - Epoxy adhesives are prepared in two steps. SN2...
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Similar questions
- which is more basic and why? pyrazole and pyridinearrow_forwardDraw the corresponding general mechanism of a tertiary amine with an acyl halide.arrow_forwarda) For the following three isomeric amines (primary, secondary, tertiary) draw the structure in the right hand boxes that represent the most basic amine and the most nucleophilic amine. NH₂ primary amine secondary amine tertiary amine most basic? most nucleophilic?arrow_forward
- 5) Imidazole is more basic than pyridine, but more acidic than pyrrole, why? N.arrow_forwardWhat products are formed when all of the amide and ester bonds are hydrolyzed in each of the following compounds? Tamiu [part (a)] is the trade name of the antiviral agent oseltamivir, thought to be the most effective agent in treating inuenza. Aspartame [part (b)] is the articial sweetener used in Equal and many diet beverages. One of the products ofthis hydrolysis reaction is the amino acid phenylalanine. Infants afflicted with phenylketonuria cannot metabolize this amino acid, so it accumulates, causing mental retardation. When the affliction is identied early, a diet limiting the consumption of phenylalanine (and compounds like aspartame that are converted to it) can make a normal life possible.arrow_forwardSee image belowarrow_forward
- When acetophenone, hydroxelamine hydrochloride, and sodium hydroxide are reacted to synthesize acetophenone oxime, why is it necessary to add hydrochloric acid after the reaction to make it acidic?arrow_forwardExplain why imidazolides are much more reactive than other amides in nucleophilic acyl substitution.arrow_forwarda) Put these three common types of carbonyl compound in order of decreasing reactivity ester amide acid chloride b) For the least reactive, show the interconversion to its other resonance form: How does this electron delocalisation make it stable? c) For the most reactive, draw the mechanism of its undergoing hydrolysis (reaction with H2O): Why makes this type of carbonyl so reactive to nucleophiles?arrow_forward
- Account for the experimental behavior of each class of amines (primary,secondary and tertiary) based on their relative reactivities with benzenesulfonyl chloride.arrow_forwardExplain the reaction for the formation of acetal and hemiacetal. Explain why N,N-disubstituted amide is less acidic than ester. Why only methyl ketone do undergoes haloform reaction. LDA is the base of choice for carbonyl compound to completely convert into enolate. Why?arrow_forward1. Why can a NaOH be used to distinguish amines and ammonium salts? Multiple choice2. In the synthesis of gabriel, phthlamide acts as? Explain(a) Catalyst(b) Reagents(c) Nucleophile(d) Electrophic 3. Amine compounds that can fade the color of the bromine solution, namely?arrow_forward
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