Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Show 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-butylamine
Predict the major products formed when benzoyl chloride (PhCOCl) reacts with the following reagents.(a) ethanol (b) sodium acetate (c) aniline
(a) How will you convert:(i) Benzene to acetophenone (ii) Propanone to 2-Methylpropan-2-ol(b) Give reasons :(i) Electrophilic substitution in benzoic acid takes place at meta position.(ii) Carboxylic acids are higher boiling liquids than aldehydes, ketones and alcohols of comparable molecular masses.(iii) Propanal is more reactive than propanone in nucleophilic addition reactions.
Chapter 20 Solutions
Organic Chemistry
Ch. 20 - Prob. 1PPCh. 20 - Prob. 2PPCh. 20 - Prob. 3PPCh. 20 - PRACTICE PROBLEM 20.5 Outline a preparation of...Ch. 20 - Prob. 5PPCh. 20 - Prob. 6PPCh. 20 - Prob. 7PPCh. 20 - Prob. 8PPCh. 20 - Prob. 9PPCh. 20 - Practice Problem 20.11 In the preceding examples...
Ch. 20 - Prob. 11PPCh. 20 - Prob. 12PPCh. 20 - Practice Problem 20.14
Outline a synthesis of...Ch. 20 - Prob. 14PPCh. 20 - Prob. 15PPCh. 20 - PRACTICE PROBLEM
20.16
An amine A has the...Ch. 20 - PRACTICE PROBLEM Sulfonamides of primary amines...Ch. 20 - PRACTICE PROBLEM
20.18 (a) Starting with aniline...Ch. 20 - Prob. 19PCh. 20 - 20.20 Give common or systematic names for each of...Ch. 20 - Which is the most basic nitrogen in each compound?...Ch. 20 - Prob. 22PCh. 20 - Prob. 23PCh. 20 - Show how you might synthesize each of the...Ch. 20 - Prob. 25PCh. 20 - 20.26 Provide the major organic product from each...Ch. 20 - Prob. 27PCh. 20 - Prob. 28PCh. 20 - Prob. 29PCh. 20 - Prob. 30PCh. 20 - Prob. 31PCh. 20 - Write equations for simple chemical rests or state...Ch. 20 - Prob. 33PCh. 20 - 20.34 Using reactions that we have studied in this...Ch. 20 - 20.35 Provide a detailed mechanism for each of the...Ch. 20 - Prob. 36PCh. 20 - Prob. 37PCh. 20 - Prob. 38PCh. 20 - Prob. 39PCh. 20 - 20.40 Give structures for compounds R-W:
Ch. 20 - Prob. 41PCh. 20 - Prob. 42PCh. 20 - Diethylpropion (shown here) is a compound used in...Ch. 20 - Prob. 44PCh. 20 - 20.45 Compound W is soluble in dilute aqueous HCI...Ch. 20 - 20.46 Propose structures for compounds X, Y, and...Ch. 20 - Compound A(C10H15N) is soluble in dilute HCI. The...Ch. 20 - Prob. 48PCh. 20 - Prob. 49PCh. 20 - 20.52 When phenyl isochiocyanatc, , is reduced...Ch. 20 - Prob. 51PCh. 20 - 20.54 Propose a mechanism that can explain the...Ch. 20 - When acetone is treated with anhydrous ammonia in...Ch. 20 - Prob. 54PCh. 20 - Which of the following would be soluble in dilute...Ch. 20 - Which would yield propylamine? (d) Two of the...Ch. 20 - Select the reagent from the list below that could...Ch. 20 - Prob. 4QCh. 20 - 20.5 Select the stronger base from each pair (in...
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Similar questions
- Predict the products from the reactions of the following amines with sodium nitrite indilute HCl.(a) cyclohexanaminearrow_forward(a) Account for the following :(i) Propanal is more reactive than propanone towards nucleophilic reagents.(ii) Electrophilic substitution in benzoic acid takes place at meta position.(iii) Carboxylic acids do not give characteristic reactions of carbonyl group.(b) Give simple chemical test to distinguish between the following pairs of compounds:(i) Acetophenone and benzaldehyde(ii) Benzoic acid and ethylbenzoate.arrow_forwardDraw line structures of the following compounds and the product you would obtain from the reduction of each.(a) Isopropyl methyl ketone (b) p-Hydroxybenzaldehyde(c) 2-Methylcyclopentanonearrow_forward
- (a) Although phenoxide ion has more number of resonating structures than carboxylate ion, carboxylic acid is a stronger acid than phenol. Give two reasons.(b) How will you bring about the following converstions?(i) Propanone to propane (ii) Benzoyl chloride to benzaldehyde(iii) Ethanal to but-2-enalarrow_forward(a) Draw the structures of the following compounds :(i) 4-Chloropentan-2-one (ii) p-Nitropropiophenone(b) Give tests to distinguish between the following pairs of compounds :(i) Ethanal and Propanal (ii) Phenol and Benzoic acid(iii) Benzaldehyde and Acetophenonearrow_forward(D)The best route to synthesise aromatic primary amines is by reduction of the corresponding nitro compounds. Draw the reaction scheme for the preparation of p-toluidine.arrow_forward
- How will you convert the following :(i) Nitrobenzene into aniline(ii) Ethanoic acid into methanamine(iii) Aniline into N-phenylethanamide(Write the chemical equations involved)arrow_forwardWrite down the reaction of acetaldehyde with the following. (a) Tollens' reagent (b) 2,4-dinitrophenylhydrazine (c) I2 / NaOHarrow_forwardPredict the products formed when cyclohexanone reacts with the following reagents. (k) sodium cyanide (l) acidic hydrolysis of the product from (k)arrow_forward
- Please help me with both of these, I am very confused and would like to studyarrow_forwarda) What are the difficulties with the following reaction to synthesize an amine. + HBr Br + NH3 NH2 b) Show a possible alternatives to this synthesis.arrow_forwardWrite a structural formula for each of the following compounds: (a) m-Chlorobenzoyl chloride (b) Trifluoroacetic anhydride (c) cis-1,2-Cyclopropanedicarboxylic anhydride (d) Ethyl cycloheptanecarboxylate (e) 1-Phenylethyl acetate (f) 2-Phenylethyl acetate (g) p-Ethylbenzamide (h) N-Ethylbenzamide (i) 2-Methylhexanenitrilearrow_forward
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