Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Question
Chapter 24.6, Problem 9P
Interpretation Introduction
Interpretation:
To write the mechanism of the last step in Gabriel
Concept introduction:
An imide (-CoNHCo-) is similar to a β- keto ester, in that the acidic N-H hydrogen is flanked by two carbonyl groups.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
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
b)Congo Red indicator is synthesized via coupling reaction of diazonium salt which is
obtained by the reaction of a primary amine and nitrous acid at 0°C. Draw the
structures of the starting materials for the synthesis in the boxes.
HO;S
SO3
N-
OH
N-
NH2
H2N
Congo Red
Diazonium salt
Amine derivative
Show how to synthesize the following amines from the indicated starting materials byacylation–reduction. b) N-benzylaniline from aniline
Chapter 24 Solutions
Organic Chemistry
Ch. 24.1 - Name the following compounds:Ch. 24.1 - Prob. 2PCh. 24.1 - Prob. 3PCh. 24.3 - Prob. 4PCh. 24.3 - The benzylammonium ion (C6H5CH2NH3+) has pKa =...Ch. 24.4 - Prob. 6PCh. 24.5 - Prob. 7PCh. 24.6 - Prob. 8PCh. 24.6 - Prob. 9PCh. 24.6 - Show two methods for the synthesis of dopamine, a...
Ch. 24.6 - Prob. 11PCh. 24.6 - Prob. 12PCh. 24.6 - Prob. 13PCh. 24.7 - Prob. 14PCh. 24.7 - Prob. 15PCh. 24.8 - Prob. 16PCh. 24.8 - Propose syntheses of the following compounds from...Ch. 24.8 - How would you prepare the following compounds from...Ch. 24.8 - Prob. 19PCh. 24.9 - Draw an orbital picture of thiazole. Assume that...Ch. 24.9 - Prob. 21PCh. 24.9 - Prob. 22PCh. 24.9 - Which nitrogen atom in the hallucinogenic indole...Ch. 24.9 - Prob. 24PCh. 24.10 - Prob. 25PCh. 24.SE - Name the following amines, and identify each as...Ch. 24.SE - The following compound contains three nitrogen...Ch. 24.SE - Name the following amine, including R, S...Ch. 24.SE - Prob. 29VCCh. 24.SE - Predict the product(s) for each reaction below and...Ch. 24.SE - Predict the product(s) and provide the complete...Ch. 24.SE - Prob. 32MPCh. 24.SE - Predict the product(s) and provide the mechanism...Ch. 24.SE - The diazotization of aniline first involves the...Ch. 24.SE - Prob. 35MPCh. 24.SE - Prob. 36MPCh. 24.SE - Prob. 37MPCh. 24.SE - Prob. 38MPCh. 24.SE - Choline, a component of the phospholipids in cell...Ch. 24.SE - Prob. 40MPCh. 24.SE - -Amino acids can be prepared by the Strecker...Ch. 24.SE - Prob. 42MPCh. 24.SE - Prob. 43MPCh. 24.SE - Prob. 44MPCh. 24.SE - Propose a mechanism for the following reaction:Ch. 24.SE - Prob. 46MPCh. 24.SE - Name the following compounds:Ch. 24.SE - Prob. 48APCh. 24.SE - Prob. 49APCh. 24.SE - Prob. 50APCh. 24.SE - Histamine, whose release in the body triggers...Ch. 24.SE - Prob. 52APCh. 24.SE - Prob. 53APCh. 24.SE - Prob. 54APCh. 24.SE - Prob. 55APCh. 24.SE - Prob. 56APCh. 24.SE - Prob. 57APCh. 24.SE - Prob. 58APCh. 24.SE - Prob. 59APCh. 24.SE - Prob. 60APCh. 24.SE - Show the products from reaction of p-bromoaniline...Ch. 24.SE - Prob. 62APCh. 24.SE - How would you prepare the following compounds from...Ch. 24.SE - Prob. 64APCh. 24.SE - Phenacetin, a substance formerly used in...Ch. 24.SE - Prob. 66APCh. 24.SE - Draw the structure of the amine that produced the...Ch. 24.SE - Fill in the missing reagents a-e in the following...Ch. 24.SE - Prob. 69APCh. 24.SE - Prob. 70APCh. 24.SE - Deduce the structure of the compound with formula...Ch. 24.SE - Prob. 72APCh. 24.SE - Prob. 73APCh. 24.SE - Prob. 74APCh. 24.SE - Prob. 75APCh. 24.SE - Prob. 76APCh. 24.SE - Propose a structure for the product with formula...Ch. 24.SE - Prob. 78APCh. 24.SE - Prob. 79APCh. 24.SE - Prob. 80APCh. 24.SE - Prob. 81APCh. 24.SE - Prob. 82APCh. 24.SE - Prob. 83APCh. 24.SE - Prob. 84AP
Knowledge Booster
Similar questions
- Define the Mechanism - Conversion of Carboxylic Acids to Amides with DCCarrow_forwardCan pyridine form a diazonium salt and can quinoline and isoquinoline undergo electrophilic substitution on the benzenoid ring but nucleophilic substitution on the nitrogen ring?arrow_forwardShow how acid derivatives hydrolyze to carboxylic acids under either acidic or basicconditions. Explain why some acid derivatives (amides, for example) require muchstronger conditions for hydrolysis than other derivatives.arrow_forward
- Excess ammonia must be used when a primary amine is synthesized by reductive amination. What product will be obtained if the reaction is carried out with excess carbonyl compound?arrow_forwardThe mechanism for acidic hydrolysis of a nitrile resembles the basic hydrolysis, exceptthat the nitrile is first protonated, activating it toward attack by a weak nucleophile (water).Under acidic conditions, the proton transfer (tautomerism) involves protonation on nitrogen followed by deprotonation on oxygen. Propose a mechanism for the acid-catalyzedhydrolysis of benzonitrile to benzamide.arrow_forwardOn the basis of the general mechanism for amide hydrolysis in acidic solution shown in Mechanism 20.4, write an analogous sequence of steps for the hydrolysis of acetanilide.arrow_forward
- An alternative procedure for preparing the amine of Step 3 is reductive amination of the corresponding ketone. What is reductive amination? Why might this two-step route for formation of the amine be preferred over the one-step reductive amination?arrow_forwardShow how you might utilize the reduction of an amide, oxime, or a nitrile to carry out each of the following transformations (a)Benzoic acid to N-ethyl-N-benzylamine (b)1-Bromopentane to hexylamine (c)Propanoic acid to tripropylamine (d)2-Butanone to sec-butylaminearrow_forwardDraw a mechanism for the following acid catalysed hydrolysis reaction. Explain verbally within your group why the equilibrium lies towards the products. You should consider both enthalpy and entropy effects in your answer. MeO Me OMe + 2 H₂O — Me OH + 3 MeOHarrow_forward
- Show how to synthesize the following amines from the indicated starting materials byreductive amination. ) N-cyclohexylaniline from cyclohexanonearrow_forwardFrom the given structures which is(a) amide that will release a secondary amine upon hydrolysis? (b) product of hydrolysis of MSO (c) a tertiary amide and (d) a diketonearrow_forwardi) What property of amines is responsible for their being basic ii) Arrange the following compounds in order of increasing basic strength putting the least basic first. NH3 CH,CONH; O NH2 CH,CH;NH; D C. c) What general name is given to the reaction between phenylamine and nitrous acid at 5°C ii) Write the equation for the reaction in c(i). + Ajouter une légende.. > Statut (Personnalisé)arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning