Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Textbook Question
Chapter 17, Problem 16PP
Practice Problem 17.15
Using decarboxylation reactions, outline a synthesis of each of the following from appropriate starting materials:
(a) 2-Hexanone
(b) 2-Methylbutanoic acid
(c) Cyclohexanone
(d) Pentanoic acid
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(a) How will you obtain the following :(i) Benzaldehyde from Phenol (ii) Benzoic acid from Aniline(b) Give reasons :(i) Aldehydes are more reactive than ketones towards nucleophilic reagents.(ii) Electrophilic substitution in benzoic acid takes place at meta position.(iii) Carboxylic acids do not give the characteristic reactions of carbonyl group.
Provide reagents
Starting exactly with any acid chloride with exactly with 5 carbon atoms, and using appropriate reagents outline the synthesis of the following molecules:
(a) 2,6-dimethyl-4-heptanone
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Chapter 17 Solutions
Organic Chemistry
Ch. 17 - Practice Problem 17.1 Give an IUPAC systematic...Ch. 17 - Prob. 2PPCh. 17 - PRACTICE PROBLEM
17.3 Which acid of each pair...Ch. 17 - Practice Problem 17.3 Write structural formulas...Ch. 17 - Practice Problem 17.4
Show how each of the...Ch. 17 - Practice Problem 17.5
Show how you could prepare...Ch. 17 - Practice Problem 17.6
(a) Which of the carboxylic...Ch. 17 - Prob. 8PPCh. 17 - Prob. 9PPCh. 17 - Practice Problem 17.9
Esters can also be...
Ch. 17 - Prob. 11PPCh. 17 - Prob. 12PPCh. 17 - Practice Problem 17.12
What products would you...Ch. 17 - Practice Problem 17.13 (a) Provide the reagents...Ch. 17 - Prob. 15PPCh. 17 - Practice Problem 17.15 Using decarboxylation...Ch. 17 - Practice Problem 17.16 Diacyl peroxides, ,...Ch. 17 - Prob. 18PCh. 17 - Give an IUPAC systematic or common name for each...Ch. 17 - Prob. 20PCh. 17 - Prob. 21PCh. 17 - 17.21 What major organic product would you expect...Ch. 17 - Prob. 23PCh. 17 - Prob. 24PCh. 17 - Prob. 25PCh. 17 - Prob. 26PCh. 17 - 17.26 What products would you expect to obtain...Ch. 17 - Write structural formulas for the major organic...Ch. 17 - 17.28 Indicate reagents that would accomplish each...Ch. 17 - Write structural formulas for the major organic...Ch. 17 - Prob. 31PCh. 17 - Prob. 32PCh. 17 - Prob. 33PCh. 17 - 17.33 On heating,...Ch. 17 - Prob. 35PCh. 17 - Prob. 36PCh. 17 - 17.36 Show how pentanoic acid can be prepared from...Ch. 17 - 17.37 The active ingredient of the insect...Ch. 17 - Prob. 39PCh. 17 - Prob. 40PCh. 17 - Give stereochemical formulas for compounds AQ:...Ch. 17 - 17.41 -Glyceraldehyde can be transformed into...Ch. 17 - Prob. 43PCh. 17 - 17.44 Cantharidin is a powerful vesicant that can...Ch. 17 - Prob. 45PCh. 17 - 17.44 Given here are the NMR spectra and carbonyl...Ch. 17 - Compound X (C7H12O4) is insoluble in aqueous...Ch. 17 - 17.45 Compound Y dissolves slowly when warmed...Ch. 17 - Prob. 49PCh. 17 - Prob. 50PCh. 17 - 17.52 Starting with 1-naphthol, suggest an...Ch. 17 - Suggest a synthesis of ibuprofen (Section 5.11)...Ch. 17 - Prob. 53PCh. 17 - Prob. 54PCh. 17 - Prob. 1LGPCh. 17 - Prob. 2LGPCh. 17 - Prob. 3LGPCh. 17 - Prob. 4LGPCh. 17 - Prob. 1QCh. 17 - 17.2 Which of the following would yield...Ch. 17 - 17.3 Which reagent would serve as the basis for a...Ch. 17 - Prob. 4QCh. 17 - Complete the following synthesis.Ch. 17 - 17.6 Which of these acids would undergo...
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- (b) State the reagents needed to convert benzoic acid into the following compounds. (i) C6H§COCI (ii) C,H$CH2OH (iii) C6H$CONHCH3arrow_forward(c) Arrange the following compounds in order of increasing acidity, and explain the reasons fo your choice of order: phenol, cyclohexanol, 2-fluorocyclohexanol, 2-fluoronhenolarrow_forwardGive the structure of the product formed on reaction of ethyl acetoacetate with each of the following: (a) 1-Bromopentane and sodium ethoxide (b) Saponification (basic hydrolysis) and decarboxylation of the product in part (a) (c) Methyl iodide and the product in part (a) treated with sodium ethoxide (d) Saponification and decarboxylation of the product in part (c) (e) 1-Bromo-3-chloropropane and one equivalent of sodium ethoxide (f) Product in part (e) treated with a second equivalent of sodium ethoxide (g) Saponification and decarboxylation of the product in part (f) (h) Phenyl vinyl ketone and sodium ethoxide (i) Saponification and decarboxylation of the product in part (h)arrow_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) Explain the mechanism of a nucleophilic attack on the carbonyl group of an aldehyde or a ketone.(b) An organic compound (A) (molecular formula CgH16Q2) was hydrolysed with dilute sulphuric acid to give a carboxylic acid (B) and an alcohol (C). Oxidation of (C) with chromic acid also produced (B). On dehydration (C) gives but-1-ene. Write the equations for the reactions involved.arrow_forwardPredict the major products formed when benzoyl chloride (PhCOCl) reacts with the following reagents.(a) ethanol (b) sodium acetate (c) anilinearrow_forward
- Each of the following reactions has been carried out under conditions such that disubstitution or trisubstitution occurred. Identify the principal organic product in each case. (a) Nitration of p-chlorobenzoic acid (dinitration) (b) Bromination of aniline (tribromination) (c) Bromination of o-aminoacetophenone (dibromination) (d) Bromination of p-nitrophenol (dibromination) (e) Reaction of biphenyl with tert-butyl chloride and iron(III) chloride (dialkylation) (f) Sulfonation of phenol (disulfonation)arrow_forwardWhich is the stronger acid in each of the following pairs? Explain your reasoning. (a) Phenol or p-hydroxybenzaldehyde (b) m-Cyanophenol or p-cyanophenol (c) o-Fluorophenol or p-fluorophenolarrow_forward(c) Arrange the following compounds in order of increasing acidity, and explain the reasons for your choice of order: phenol, cyclohexanol, 2-fluorocyclohexanol, 2-fluorophenol.arrow_forward
- Predict the major organic product of each of the following reactions.arrow_forwardRank the compounds in each of the following groups in order of their reactivity to electrophilic substitution: (a) Nitrobenzene, phenol, toluene, benzene (b) Phenol, benzene, chlorobenzene, benzoic acid (c) Benzene, bromobenzene, benzaldehyde, anilinearrow_forwardIn an aqueous solution containing sodium bicarbonate, aniline reacts quickly withbromine to give 2,4,6-tribromoaniline. Nitration of aniline requires very strong conditions,however, and the yields (mostly m-nitroaniline) are poor.(a) What conditions are used for nitration, and what form of aniline is present under theseconditions?arrow_forward
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