Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Textbook Question
Chapter 15, Problem 3PP
PRACTICE PROBLEM 15.3
Outline all steps in a reasonable mechanism for the formation of isopropylbenzene from propene and benzene in liquid HF (just shown). Your mechanism must account for the product being isopropylbenzene, not propylbenzene.
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Students have asked these similar questions
11:43
Q1.
(a)
(c)
(d)
(b) Two stereoisomers of but-2-ene are formed when 2-bromobutane reacts with
ethanolic potassium hydroxide.
(i) Explain what is meant by the term stereoisomers.
Library
Name and outline a mechanism for the reaction of 2-bromo-2-methylpropane with
ethanolic potassium hydroxide to form the alkene 2-methylpropene, (CH3)2C=CH₂
Name of mechanism
Mechanism
(ii)
Draw the structures and give the names of the two stereoisomers of
but-2-ene.
Stereoisomer 1
Name
(iii) Name this type of stereoisomerism.
Select
Name
Stereoisomer 2
When 2-bromo-2-methylpropane reacts with aqueous potassium hydroxide,
2-methylpropan-2-ol is formed as shown by the following equation.
CH3
H₂C-C-CH3 + KOH
Br
Page 2 of 14
CH3
H3C-C-CH3 + KBr
ОН
State the role of the hydroxide ions in this reaction.
Write an equation for the reaction that occurs when CH3CH₂CH₂CH₂Br reacts with
an excess of ammonia. Name the organic product of this reaction.
Equation
Name of product
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(b)
acid, HNO3 to produce compound L. The reaction of compound L with
bromine, Br2 in the presence of iron tribromide, FeBr3 produced compound
M. Benzene also undergoes Fridel-crafts alkylation reaction with
chloroethane, CH;CH2CI using catalyst N to produce compound P.
Benzene, CeHe undergoes substitution reaction with concentrated nitric
Benzena, CsHe menjalani tindak balas penukargantian dengan asid nitrik,
HNO, pekat untuk menghasilkan sebatian L. Tindak balas sebatian L
dengan bromin, Brz dengan kehadiran ferum tribromida, FeBrs
menghasilkan sebatian M. Benzena juga menjalani tindak balas alkilasi
Fridel-crafts dengan kloroetana, CH3CH2CI dengan menggunakan
pemangkin N untuk menghasilkan sebatian P.
(i)
Draw the structural formula of L, M and P.
Lukiskan formula struktur bagi sebatian L, M dan P.
(ii)
State catalyst N.
Nyatakan pemangkin N.
(iii) Show the formation of electrophile that will be reacted with benzene for the
formation of compound P.
Write the structure of the major organic product formed in the reaction of 1-pentene with each of the following: (a) Hydrogen chloride (b) Dilute sulfuric acid (c) Diborane in diglyme, followed by basic hydrogen peroxide (d) Bromine in carbon tetrachloride (e) Bromine in water (f) Peroxyacetic acid (g) Ozone (h) Product of part (g) treated with zinc and water (i) Product of part (g) treated with dimethyl sulfide (CH3)2S
Chapter 15 Solutions
Organic Chemistry
Ch. 15 - PRACTICE PROBLEM 15.1
Show how loss of a proton...Ch. 15 - Prob. 2PPCh. 15 - PRACTICE PROBLEM 15.3
Outline all steps in a...Ch. 15 - PRACTICE PROBLEM 15.4 Provide a mechanism that...Ch. 15 - Prob. 5PPCh. 15 - Prob. 6PPCh. 15 - Prob. 7PPCh. 15 - PRACTICE PROBLEM 15.8 Write resonance structures...Ch. 15 - PRACTICE PROBLEM 15.9
Provide a mechanism for the...Ch. 15 - PRACTICE PROBLEM 15.10 The trifluoromethyl group...
Ch. 15 - PRACTICE PROBLEM 15.11
Predict the major products...Ch. 15 - PRACTICE PROBLEM 15.12 Predict the major product...Ch. 15 - PRACTICE PROBLEM 15.13
Write mechanisms for the...Ch. 15 - Prob. 14PPCh. 15 - PRACTICE PROBLEM 15.15
Suppose you needed to...Ch. 15 - PRACTICE PROBLEM 15.16 1-Fluoro-2,4-dinitrobenzene...Ch. 15 - Prob. 17PPCh. 15 - PRACTICE PROBLEM 15.18
When...Ch. 15 - PRACTICE PROBLEM 15.19 Birch reduction of toluene...Ch. 15 - Prob. 20PCh. 15 - Prob. 21PCh. 15 - What monobromination product (or products) would...Ch. 15 - 15.23 Predict the major products of the following...Ch. 15 - Prob. 24PCh. 15 - 15.25 Starting with styrene, outline a synthesis...Ch. 15 - Prob. 26PCh. 15 - 15.27 Starting with aniline, outline a synthesis...Ch. 15 - Prob. 28PCh. 15 - Propose structures for compounds GI:Ch. 15 - 2,6-Dichlorophenol has been isolated from the...Ch. 15 - Prob. 31PCh. 15 - 15.32 Give structures (including stereochemistry...Ch. 15 - Provide a detailed mechanism for each of the...Ch. 15 - 15.34 Provide a detailed mechanism for the...Ch. 15 - Prob. 35PCh. 15 - Many polycyclic aromatic compounds have been...Ch. 15 - Prob. 37PCh. 15 - Prob. 38PCh. 15 - Prob. 39PCh. 15 - Prob. 40PCh. 15 - Predict the product of the following reaction.Ch. 15 - 15.42 When m-chlorotoluene is treated with sodium...Ch. 15 - Prob. 43PCh. 15 - Prob. 44PCh. 15 - Prob. 45PCh. 15 - Prob. 46PCh. 15 - 15.47 Provide structures for compounds A and B:
Ch. 15 - Prob. 48PCh. 15 - 15.49 Treating cyclohexene with acetyl chloride...Ch. 15 - 15.50 The tert-butyl group can be used as a...Ch. 15 - 15.51 When toluene is sulfonated (concentrated )...Ch. 15 - Prob. 52PCh. 15 - 2-Methylnaphthalene can be synthesized from...Ch. 15 - Prob. 54PCh. 15 - Prob. 55PCh. 15 - Prob. 56PCh. 15 - Prob. 57PCh. 15 - Prob. 58PCh. 15 - Furan undergoes electrophilic aromatic...Ch. 15 - A C-D bond is harder to break than a C-H bond,...Ch. 15 - 15.61 Acetanilide was subjected to the following...Ch. 15 - Prob. 62PCh. 15 - Prob. 63PCh. 15 - Prob. 64PCh. 15 - When compound C, which is often used to model a...Ch. 15 - Open the molecular model file for benzyne and...Ch. 15 - The structure of thyroxine, a thyroid hormone that...Ch. 15 - Prob. 2LGPCh. 15 - 3. Deduce the structures of compounds E–L in the...
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