Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Question
Chapter 18.20, Problem 36P
Interpretation Introduction
Interpretation:
The explanation for the formation of nitrosamine from secondary
Concept Introduction:
An electrophilic substitution reaction between highly activated
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Explain why a secondary amine forms a nitrosamine rather than a diazonium ion when it reacts with anitrosonium ion.
If a quaternary ammonium ion can undergo an elimination reaction with a strong base, why can’t a protonated tertiary amine undergo the same reaction?
Rank the following amines based on basicity
Rationalize the electronic effects responsible for the basicity of amines
Chapter 18 Solutions
Organic Chemistry (8th Edition)
Ch. 18.1 - Draw the structure for each of the following: a....Ch. 18.3 - Why does hydration inactivate FeBr3?Ch. 18.6 - Prob. 4PCh. 18.7 - What is the major product of a Friedel-Crafts...Ch. 18.9 - Describe two ways to prepare each of the following...Ch. 18.10 - Prob. 7PCh. 18.11 - Name the following:Ch. 18.11 - Draw a structure for each of the following: a....Ch. 18.11 - Draw the structure for each of the following: a....Ch. 18.11 - Correct the following incorrect names: a....
Ch. 18.12 - Prob. 14PCh. 18.12 - List the compounds in each set from most reactive...Ch. 18.13 - Prob. 16PCh. 18.13 - What product(s) result from nitration of each of...Ch. 18.13 - Prob. 18PCh. 18.13 - What products are obtained from the reaction of...Ch. 18.15 - Give the products, if any, of each of the...Ch. 18.16 - a. Does a coupling reaction have to be used to...Ch. 18.16 - Show how the following compounds can be...Ch. 18.16 - Prob. 24PCh. 18.17 - What is the major product(s) of each of the...Ch. 18.17 - Prob. 26PCh. 18.18 - Why isn't FeBr3 used as a catalyst in the first...Ch. 18.18 - Prob. 29PCh. 18.18 - Write the sequence of steps required for the...Ch. 18.18 - Show how the following compounds can be...Ch. 18.19 - What product is formed from reaction of...Ch. 18.19 - Prob. 33PCh. 18.19 - Draw the structure of the activated ring and the...Ch. 18.20 - Prob. 35PCh. 18.20 - Prob. 36PCh. 18.20 - Diazomethane can be used to convert a carboxylic...Ch. 18.21 - Prob. 38PCh. 18.21 - Prob. 39PCh. 18.21 - Prob. 40PCh. 18.22 - Prob. 41PCh. 18 - Draw the structure for each of the following: a....Ch. 18 - Name the following:Ch. 18 - Prob. 44PCh. 18 - Prob. 45PCh. 18 - For each of the statements in Column I, choose a...Ch. 18 - What product is obtained from the reaction of...Ch. 18 - Draw the product(s) of each of the following...Ch. 18 - Rank the following substituted anilines from most...Ch. 18 - Prob. 50PCh. 18 - Prob. 51PCh. 18 - Show how the following compounds can be...Ch. 18 - Prob. 53PCh. 18 - The compound with the 1H NMR spectrum shown below...Ch. 18 - Rank each group of compounds from most reactive to...Ch. 18 - Prob. 56PCh. 18 - Prob. 57PCh. 18 - For each of the following components, indicate the...Ch. 18 - Prob. 59PCh. 18 - Prob. 60PCh. 18 - Describe two ways to prepare anisole from benzene.Ch. 18 - Prob. 62PCh. 18 - The following tertiary alkyl bromides undergo an...Ch. 18 - An aromatic hydrocarbon with a molecular formula...Ch. 18 - Show how the following compounds can be...Ch. 18 - Use the four compounds shown below to answer the...Ch. 18 - a. Rank the following esters from most reactive to...Ch. 18 - A mixture of 0.10 mol benzene and 0.10 mol...Ch. 18 - Prob. 69PCh. 18 - Prob. 70PCh. 18 - Benzene underwent a Friedel-Crafts acylation...Ch. 18 - Prob. 72PCh. 18 - Prob. 73PCh. 18 - Friedel-Crafts alkylations can be carried out with...Ch. 18 - Show how the following compounds can be prepared...Ch. 18 - Prob. 76PCh. 18 - Prob. 77PCh. 18 - a. Describe four ways the following reaction can...Ch. 18 - Propose a mechanism for each of the following...Ch. 18 - How can you prepare the following compounds with...Ch. 18 - Describe how naphthalene can he prepared from the...Ch. 18 - Using resonance contributors for the carbocation...Ch. 18 - Prob. 83PCh. 18 - What reagents are required to carry out the...Ch. 18 - Prob. 85PCh. 18 - Prob. 86PCh. 18 - Prob. 87PCh. 18 - Propose a mechanism for each of the following...Ch. 18 - P-Fluoronitrobenzene is more reactive toward...Ch. 18 - When heated with chromic acid, compound A forms...Ch. 18 - Show how the following compounds can be prepared...Ch. 18 - How can you distinguish the following compounds...Ch. 18 - Describe how mescaline can be synthesized from...Ch. 18 - Propose a mechanism for the following reaction...Ch. 18 - Propose a mechanism for each of the following...Ch. 18 - Describe how 3-methyl-1-phenyl-3-pentanol can he...Ch. 18 - An unknown compound reacts with ethyl chloride and...Ch. 18 - a. Explain why the following reaction leads to the...Ch. 18 - Explain why hydroxide ion catalyzes the reaction...Ch. 18 - Prob. 100PCh. 18 - Prob. 101PCh. 18 - a. How can aspirin be synthesized from benzene? b....Ch. 18 - Prob. 103PCh. 18 - Show how Novocain, a painkiller used frequently by...Ch. 18 - Prob. 105PCh. 18 - Saccharin, an artificial sweetener, is about 300...
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- Aliphatic amines are more basic than ammonia, whereas aromatic amines are less basic than ammonia. Is that true or false?arrow_forwardWhy is it that benzenesulfonamides of primary amines are more soluble in aqueous alkali than the corresponding benzamides?arrow_forwardExplain the following giving a reason in each case Why is an alkylamine more basic than ammonia? Why do primary amines have higher boiling points than the tertiary amines?arrow_forward
- What is the effect of acid on the solubility of amines that are water-insoluble based on aniline and N, N-dimethylaniline?arrow_forwardAccount for the experimental behavior of each class of amines (primary,secondary and tertiary) based on their relative reactivities with benzenesulfonyl chloride.arrow_forwardPredict the NMR spectra of Acetanilide, p-acetamidobenzene sulphonamide and p-aminobenzene sulphonamidearrow_forward
- Give reasons for the following:(i) Aniline does not undergo Friedal-Crafts reaction.(ii) (CH3)2 NH is more basic than (CH3)3 N in an aqueous solution.(iii) Primary amines have higher boiling point than tertiary amines.arrow_forwardThe hydrolysis of an amide in acidic conditions forms A. a carboxylate salt and an alcohol B. a carboxylate salt and an amine C. an alcohol and an amine salt (an ammonium ion) D. a carboxylic acid and an amine salt (an ammonium ion)arrow_forwardFor the identification tests of amines and amides. What would be the positive result of: - Hinsberg - Quinhydrone - Ramini - Alkaline hydrolysis - Acid hydrolysis - Nitrous acid testarrow_forward
- Compare the reactivity of the primary amine to secondary amines towards the synthesis of amides. synthesis of N,N-Diethyl-meta-toluamidearrow_forwardFor the identification tests of amines and amides. What would be the Test for amine/Amide for: - Hinsberg - Quinhydrone - Ramini - Alkaline Hydrolysis - Acid Hydrolysis - Nitrous acid testarrow_forwardgive the results of the following compounds after reaction with nitrous acid test a. primary aliphatic amine b. secondary aliphatic amine c. tertiary aliphatic amine d. primary aromatic aminearrow_forward
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