Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Question
Chapter 19.10C, Problem 19.14P
(a)
Interpretation Introduction
Interpretation:
A mechanism for the reaction of
(b)
Interpretation Introduction
Interpretation:
A mechanism to explain the curious result when
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 amine
2. the acid-catalyzed hydrolysis of an enamine to a carbonyl compound and a secondary amine a. How do the two mechanisms differ?
How does a reaction with aniline and benzyl
bromide work together to create dibenzylaniline?
How do these reagents contribute to the reaction?
What is their purpose?
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
Chapter 19 Solutions
Organic Chemistry (9th Edition)
Ch. 19.2A - Prob. 19.1PCh. 19.2B - Prob. 19.2PCh. 19.2B - Give correct names for the following amines:Ch. 19.3 - Prob. 19.4PCh. 19.4 - Prob. 19.5PCh. 19.6 - Rank each set of compounds in order of increasing...Ch. 19.8A - Prob. 19.7PCh. 19.8C - Prob. 19.8PCh. 19.8C - Prob. 19.9PCh. 19.8D - a. Show how fragmentation occurs to give the base...
Ch. 19.10B - Propose a mechanism for nitration of pyridine at...Ch. 19.10B - Prob. 19.12PCh. 19.10C - Prob. 19.13PCh. 19.10C - Prob. 19.14PCh. 19.11 - Propose a mechanism to show the individual...Ch. 19.11 - Prob. 19.16PCh. 19.12 - Give the products expected from the following...Ch. 19.13 - Prob. 19.18PCh. 19.13 - Prob. 19.19PCh. 19.14 - Prob. 19.20PCh. 19.15 - Prob. 19.21PCh. 19.15 - Prob. 19.22PCh. 19.16 - Prob. 19.23PCh. 19.17 - Prob. 19.24PCh. 19.17 - Prob. 19.25PCh. 19.18 - Prob. 19.26PCh. 19.19 - Prob. 19.27PCh. 19.20A - Addition of one equivalent of ammonia to...Ch. 19.20A - Prob. 19.29PCh. 19.20B - Show how you would accomplish the following...Ch. 19.20C - Prob. 19.31PCh. 19 - For each compound, 1. classify the...Ch. 19 - Prob. 19.33SPCh. 19 - Within each structure, rank the indicated...Ch. 19 - In each pair of compounds, select the stronger...Ch. 19 - Which of the following compounds are capable of...Ch. 19 - Complete the following proposed acid-base...Ch. 19 - Predict the products of the following reactions:...Ch. 19 - Prob. 19.39SPCh. 19 - Show how m-toluidine can be converted to the...Ch. 19 - The mass spectrum of tert-butylamine follows shows...Ch. 19 - Prob. 19.42SPCh. 19 - The following drugs are synthesized using the...Ch. 19 - Prob. 19.44SPCh. 19 - Synthesize from benzene. (Hint: All of these...Ch. 19 - Propose mechanisms for the following reactions.Ch. 19 - Prob. 19.47SPCh. 19 - Prob. 19.48SPCh. 19 - Prob. 19.49SPCh. 19 - Show how you can synthesize the following...Ch. 19 - Prob. 19.51SPCh. 19 - The alkaloid coniine has been isolated from...Ch. 19 - A chemist is summoned to an abandoned...Ch. 19 - Pyrrole undergoes electrophilic aromatic...Ch. 19 - Prob. 19.55SPCh. 19 - Prob. 19.56SPCh. 19 - An unknown compound shows a weak molecular ion at...Ch. 19 - A compound of formula C11H16N2 gives the IR,...Ch. 19 - (A true story.) A drug user responded to an ad...Ch. 19 - Prob. 19.60SPCh. 19 - Prob. 19.61SPCh. 19 - Prob. 19.62SPCh. 19 - Prob. 19.63SPCh. 19 - Prob. 19.64SPCh. 19 - Prob. 19.65SP
Knowledge Booster
Similar questions
- Why do you wash the dichloromethane solution of your reductive amination product with sodium bicarbonate, rather than dilute aqueous HCl? a) Sodium bicarbonate is a good method of removing aldehydes from organic solvent.b) The amine product will be protonated by acid and remain in the aqueous layer as a salt.c) Sodium bicarbonate transfers the amine starting material into the aqueous layer.d) Sodium bicarbonate reacts with leftover NaBH(OAc)3 and removes it from the mixture.arrow_forwardWhich of these statements is NOT true about the reaction of amines with a cyclic anhydride like phthalic anhydride? a. Dimethylamine will give a cyclic imide product. b. Aniline will give a cyclic imide product. c. Triethylamine will give a cyclic imide product. d. The reaction undergoes a nucleophilic acyl substitution mechanism.arrow_forwardWhich of the following reactions will not produce N-methylbutanamine? O a. Reduction of N-methylbutanamide with LIAIH4. O b. The reaction of butanoyl chloride with methanamine. OC. The reaction of methanamine with 1-butyl bromide and subsequent reaction with a strong base. O d. The reaction of 1-butanamine with methyl bromide and subsequent reaction with a strong base.arrow_forward
- What alkyl bromide would you use in a Gabriel synthesis to prepare each of the following amines? a. pentylamine b. isohexylamine c. benzylamine d. cyclohexylaminearrow_forwardWhat kinds of halides cannot be used to alkylate an amine? Why not? a.Tertiary halides form alkenes on elimination. b.Aryl halides unless activated by electron-withdrawing groups c.Halides with beta-alkyl groups are sterically hindered. d. all of the abovearrow_forward1. Create a flowchart for the synthesis and purification of phenacetin. Draw out your steps for the extraction process and label the organic and aqueous layers in your diagrams. Indicate where the product is in each step. 2. Draw the mechanism for the deprotonation of the phenol group of acetaminophen by potassium carbonate. Label the acid, base, conjugate acid and conjugate base. How do you know potassium carbonate is a strong enough base to do this deprotonation?arrow_forward
- D. Write the multistep syntheses for the following target compound. 1 ỌCH3 D. Draw stepwise mechanism for the given amide. You can use hydroxybenzotriazole (HOBt) or 1-Hydroxy-7-azabenzotriazole (HOAt) as catalyst. 1 N=C=N NH₂ y for osos NH₂ Diisopropylcarbodiimide (DIC)arrow_forwardShow how to synthesize the following amines from the indicated starting materials below. Each of the final products may require several sequential steps. Draw the structure for each of the steps and show the reagents required. Starting material Final product b) Benzene m-bromoaniline c) ethylbenzene p-ethylaniline + o-ethylaniline d) benzene p-bromoaniline + o-bromoanilinearrow_forward1. Which are the starting materials used to synthesize the given compound through reductive amination? a. propan-1-amine and acetone b. acetone and dimethylamine c. propanal and dimethylmine d. propan-1-amine and acetaldehyde 2. Arrange the following in increasing order of acidity. I. 2,3-Dichlorobutanoic acid II. 2,2-Dichlorobutanoic acid III. 2-Chlorobutanoic acid IV. Butanoic acid a. Ilarrow_forwardHow do you account for the fact that N-phenylacetamide (acetanilide) is less reactive toward electrophilic aromatic substitution than is aniline? -NHCCH, -NH, N-Phenylacetamide (Acetanilide) Anilinearrow_forward14. What products result from the reaction between water and the following amine: a. butyl ethyl methyl ammonium ion + OH+ b. butyl ethyl methyl ammonium ion + H3O+ c. butyl ethyl methyl ammonium ion + H3O d. butyl ethyl methyl ammonium ion + OH- e. butyl ethyl methyl ammonium ion + H2Oarrow_forwardWhat is the reason of providing a mild acid condition for the preparation of imine? Mild acid will protonate the hydroxyl group of the aminoalcohol intermediate without protonating the nitrogen of the amine starting materials. O Strong acid will rapidly neutralize the amine starting materials before any reaction can occur. Strong acid condition will alter the structure of aldehyde or ketone as the strong acid will attach to the carbonyl oxygen of aldehyde or ketone making it least nucleophilic. Mild acid will protonate the aldehyde and ketones readily rather than the strong acid.arrow_forwardarrow_back_iosSEE MORE QUESTIONSarrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning