Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
expand_more
expand_more
format_list_bulleted
Question
Chapter 11.10, Problem 38P
Interpretation Introduction
Interpretation:
The reason should be explained for the protonated tertiary
Concept introduction:
Hofmann elimination:
Quartnary ammonium ion undergoes an elimination, when using strong base like hydroxide ion this reaction is called as hofmann elimination.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
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?
Following are structural formulas for two more widely used sulfonylurea hypoglycemic agents.Show how each might be synthesized by converting an appropriate amine to a carbamic ester and then treating the carbamate with the sodium salt of a substituted benzenesulfonamide.
Account for the experimental behavior of each class of amines (primary,secondary and tertiary) based on their relative reactivities with benzenesulfonyl chloride.
Chapter 11 Solutions
Organic Chemistry
Ch. 11.1 - Why are NH3 and CH3NH2 no longer nucleophiles when...Ch. 11.1 - Prob. 2PCh. 11.1 - Prob. 5PCh. 11.2 - Prob. 7PCh. 11.3 - Prob. 9PCh. 11.3 - Show how 1-propanol can be converted into the...Ch. 11.4 - Which of the following alcohols dehydrates the...Ch. 11.4 - Prob. 12PCh. 11.4 - Prob. 13PCh. 11.4 - Propose a mechanism for each of the following...
Ch. 11.4 - Draw the product of each of the following...Ch. 11.4 - Explain why the following alcohols, when heated...Ch. 11.4 - What stereoisomers are formed in the following...Ch. 11.4 - Prob. 18PCh. 11.4 - What alcohol would you treat with phosphorus...Ch. 11.5 - Prob. 20PCh. 11.6 - Prob. 22PCh. 11.7 - Prob. 24PCh. 11.7 - Would you expect the reactivity of a five-membered...Ch. 11.7 - Prob. 26PCh. 11.7 - What products are obtained from the reaction of...Ch. 11.7 - Prob. 28PCh. 11.7 - Prob. 29PCh. 11.7 - Prob. 30PCh. 11.8 - Prob. 31PCh. 11.8 - Prob. 32PCh. 11.8 - How do the major products obtained from...Ch. 11.8 - Explain why the two arene oxides in Problem 38...Ch. 11.8 - Three arene oxides can be obtained from...Ch. 11.9 - Explain why the half-life (the time it takes for...Ch. 11.10 - Prob. 38PCh. 11.10 - Prob. 39PCh. 11.10 - Prob. 40PCh. 11.10 - Prob. 41PCh. 11.10 - Prob. 42PCh. 11.11 - Using an alkyl halide and a thiol as starting...Ch. 11.11 - The following three nitrogen mustards were studied...Ch. 11.11 - Why is melphalan a good cancer drug?Ch. 11.11 - Prob. 47PCh. 11 - Prob. 48PCh. 11 - Which compound is more likely to be carcinogenic?Ch. 11 - Prob. 50PCh. 11 - Prob. 51PCh. 11 - Write the appropriate reagent over each arrow.Ch. 11 - What alkenes would you expect to be obtained from...Ch. 11 - Prob. 54PCh. 11 - When heated with H2SO4, both...Ch. 11 - What is the major product obtained from the...Ch. 11 - When deuterated phenanthrene oxide undergoes a...Ch. 11 - An unknown alcohol with a molecular formula of...Ch. 11 - Prob. 59PCh. 11 - Prob. 60PCh. 11 - Propose a mechanism for the following reaction:Ch. 11 - What product would be formed if the four-membered...Ch. 11 - Which of the following ethers would be obtained in...Ch. 11 - Using the given starting material any necessary...Ch. 11 - Prob. 65PCh. 11 - When 3-methyl-2-butanol is heated with...Ch. 11 - Propose a mechanism for each of the following...Ch. 11 - How could you synthesize isopropyl propyl ether,...Ch. 11 - When the following seven-membered ring alcohol is...Ch. 11 - Ethylene oxide reacts readily with HO because of...Ch. 11 - Prob. 71PCh. 11 - Propose a mechanism for each of the following...Ch. 11 - Explain why the acid-catalyzed dehydration of an...Ch. 11 - Triethylene glycol is one of the products obtained...Ch. 11 - Prob. 75PCh. 11 - Prob. 76PCh. 11 - When ethyl ether is heated with excess HI for...Ch. 11 - Propose a mechanism for the following reaction:Ch. 11 - Prob. 79PCh. 11 - An ion with a positively charged nitrogen atom in...Ch. 11 - Propose a mechanism for each of the following...Ch. 11 - Prob. 82PCh. 11 - The following reaction takes place several times...Ch. 11 - A vicinal diol has OH groups on adjacent carbons....Ch. 11 - Prob. 85PCh. 11 - Prob. 86PCh. 11 - Two stereoisomers are obtained from the reaction...Ch. 11 - Propose a mechanism for each or the following...Ch. 11 - Triethylenemelamine (TEM) is an antitumor agent....
Knowledge Booster
Similar questions
- Indicate whether the following statement is true or false. Aliphatic amines are more basic than ammonia, whereas aromatic amines are less basic than ammonia. When amines are reacted with bases, they form ammonium salts. Benzenesulfonyl chloride or p-toluenesulfonylchloride give N-substituted sulfonamides with primary and secondary amines. Derivative of primary amines is insoluble in dilute NaOHarrow_forwardExplain why a secondary amine forms a nitrosamine rather than a diazonium ion when it reacts with anitrosonium ion.arrow_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
- The 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_forwardCompare the reactivity of the primary amine to secondary amines towards the synthesis of amides. synthesis of N,N-Diethyl-meta-toluamidearrow_forwardWhat amides will form attached amine on treatment with LiAlH4 ?arrow_forward
- Features of the structure of imino acids. Formation of amides from amino acids.arrow_forwardAliphatic amines are more basic than ammonia, whereas aromatic amines are less basic than ammonia. Is that true or false?arrow_forwardWhich of these amines would produce the salt with the highest melting point if mixed separately with hydrochloric acid (HCl)? Based on the structure and properties of the resulting ammonium salts, explain your reasoningarrow_forward
arrow_back_ios
arrow_forward_ios
Recommended textbooks for you
- Chemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage LearningMacroscale and Microscale Organic ExperimentsChemistryISBN:9781305577190Author:Kenneth L. Williamson, Katherine M. MastersPublisher:Brooks ColeOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
Macroscale and Microscale Organic Experiments
Chemistry
ISBN:9781305577190
Author:Kenneth L. Williamson, Katherine M. Masters
Publisher:Brooks Cole
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning