Organic Chemistry, Loose-leaf Version
8th Edition
ISBN: 9781305865549
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Textbook Question
Chapter 11.5, Problem 11.6P
Draw structural formulas for the major products of each reaction.
(a)
(b)
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1. (a) Describe aromaticity, Kekule structure and resonance structure for benzene.
(b) Why is benzene more stable than aliphatic alkenes?
Describe how would you distinguish the following pairs,
(a) Benzene and cyclohexane
(b) Phenol and toluene
(c) Phenol and benzoic acid
6. Describe concisely a chemical test to distinguish between the following pairs of
compounds.
(a)
n-pentanol and 3-methylpentan-3-ol
(b)
Ethanal dan pentanal
(c)
Phenol and benzoic acid
Chapter 11 Solutions
Organic Chemistry, Loose-leaf Version
Ch. 11.2 - Write IUPAC and common names for these ethers. (a)...Ch. 11.3 - Arrange these compounds in order of increasing...Ch. 11.4 - Show how you might use the Williamson ether...Ch. 11.4 - Show how ethyl hexyl ether might be prepared by a...Ch. 11.5 - Account for the fact that treatment of tert-butyl...Ch. 11.5 - Draw structural formulas for the major products of...Ch. 11.6 - Prob. 11.7PCh. 11.8 - Draw the expected products of Sharpless...Ch. 11.9 - Prob. AQCh. 11.9 - Prob. BQ
Ch. 11.9 - Prob. CQCh. 11.9 - Prob. DQCh. 11 - Write names for these compounds. Where possible,...Ch. 11 - Prob. 11.11PCh. 11 - Each compound given in this problem is a common...Ch. 11 - Account for the fact that tetrahydrofuran (THF) is...Ch. 11 - Prob. 11.14PCh. 11 - Write equations to show a combination of reactants...Ch. 11 - Propose a mechanism for this reaction.Ch. 11 - Prob. 11.17PCh. 11 - Prob. 11.18PCh. 11 - Prob. 11.19PCh. 11 - Prob. 11.20PCh. 11 - Ethylene oxide is the starting material for the...Ch. 11 - Prob. 11.22PCh. 11 - Predict the structural formula of the major...Ch. 11 - The following equation shows the reaction of...Ch. 11 - Propose a mechanism to account for this...Ch. 11 - Acid-catalyzed hydrolysis of the following epoxide...Ch. 11 - Prob. 11.27PCh. 11 - Prob. 11.28PCh. 11 - Prob. 11.29PCh. 11 - Propose a mechanism for the following...Ch. 11 - Show reagents and experimental conditions to...Ch. 11 - Starting with cis-3-hexene, show how to prepare...Ch. 11 - Show reagents to convert cycloheptene to each of...Ch. 11 - Show reagents to convert bromocyclopentane to each...Ch. 11 - Prob. 11.35PCh. 11 - Starting with acetylene and ethylene oxide as the...Ch. 11 - Following are the steps in the industrial...Ch. 11 - Prob. 11.38PCh. 11 - Prob. 11.39PCh. 11 - Aldehydes and ketones react with one molecule of...Ch. 11 - Prob. 11.42PCh. 11 - Write the products of the following sequences of...Ch. 11 - Using your reaction roadmap as a guide, show how...Ch. 11 - Using your reaction roadmap as a guide, show how...Ch. 11 - Using your reaction roadmap as a guide, show how...Ch. 11 - During the synthesis of the antiasthmatic drug...Ch. 11 - Prob. 11.48P
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- (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_forwardProvide IUPAC names for the following compounds. (a) -OH (b)arrow_forwardDescribe how would you distinguish the following pairs, (a) Benzene and cyclohexane (b) Phenol and toluene (c) Phenol and benzoic acid (d) methanol and isopropyl alcoholarrow_forward
- (a) Compound D undergoes a reaction with hydrogen bromide, HBr to produce 2-bromobutane. D exists as cis-trans isomers and decolourises bromine solution in methylene chloride, CH2CI2. (i) Draw and name the structure of compound D. (ii) Draw two (2) constitutional isomers of compound D.arrow_forwardThe cis ketone A is isomerized to a trans ketone B with aqueous NaOH. A similar isomerization does not occur with ketone C. (a) Draw the structure of B using a chair cyclohexane. (b) Label the substituents in C as cis or trans, and explain the difference in reactivity.arrow_forward(ii) Name the following using IUPAC system of nomenclature: (a) CH2 (Cl) CH (NH2) CHO (b) CH3 C (Br) CH2 CH (F) COOH Brarrow_forward
- For each pair of compounds, predict which compound has a higher boiling point. then explain why that compound has a higher boiling point. (a) isopropyl bromide and n-butyl bromide (b) isopropyl chloride and tert-butyl bromide (c) 1-bromobutane and 1-chlorobutanearrow_forwardPredict the major products formed when benzoyl chloride (PhCOCl) reacts with the following reagents.(a) ethanol (b) sodium acetate (c) anilinearrow_forward(a) Give chemical tests to distinguish between(i) Phenol and Benzoic acid (ii) Benzophenone and Acetophenonearrow_forward
- Write the reagent or draw structures of the starting material or organic product(s) in the following reactions. If more than one product is formed, identify the major product where possible. (a) (b) HO OH OH H2SO4 ? Cl₂ ? FeCl3arrow_forward6) Which is the organic product for the following reaction? (a) (b) (c) (d) сон COOH ОН ОН COOH COOH KMnO4 H2Oarrow_forwardPredict the major products formed when benzoyl chloride (PhCOCl) reacts with the following reagents.(a) ethanoarrow_forward
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