Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Question
Chapter 11.SE, Problem 41AP
Interpretation Introduction
Interpretation:
The faster reactant is to be identified from SN2 reaction with OH-.
Concept introduction:
SN2 reaction:
Tosylated compound is reaction with sodium methoxide which undergoes again SN2 type of reaction, the methoxide ion attacks the carbon atom through the back side and provides Inverse configuration of methoxy compound. This is shown below,
Given information:
a.
The given compound is shown below,
CH3I and CH3Br
b.
The given compound is shown below,
CH3CH2I in ethanol and CH3CH2I in dim ethylsulf oxide (DMSO)
c.
The given compound is shown below,
(CH3)3CCl and CH3Cl
d.
The given compound is shown below,
CH2 = CH2 Br or CH2 = CHCH2Br
Expert Solution & Answer
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1. Which reaction in each of these pairs would you expect to be faster?a. The SN2 displacement by iodide ion on CH3Cl or on CH3Tosb. The SN2 displacement by acetate ion on bromoethane or onbromocyclohexanec. The SN2 displacement on 2-bromopropane by ethoxide ion or bycyanide ion
The following questions ask you to choose which of the pair reactions shown has been correctly identified as faster. Choose all correct answers
In the SN2 displacement by iodide of CH3Cl or of CH3OTs, CH3OTs reacts faster.
In the SN2 displacement by acetate of bromoethane or bromocyclohexane, bromocyclohexane reacts faster.
In the SN2 displacement by CH3CH2O- or by CN- on 2-bromopropane, CN- reacts faster.
In the SN2 displacement by HC≡C- on bromomethane in benzene or in acetonitrile, reaction in acetonitrile goes faster.
Which of the following compounds reacts with HBr more rapidly?
Chapter 11 Solutions
Organic Chemistry
Ch. 11.1 - Prob. 1PCh. 11.2 - Prob. 2PCh. 11.2 - Prob. 3PCh. 11.3 - Prob. 4PCh. 11.3 - Prob. 5PCh. 11.3 - Rank the following compounds in order of their...Ch. 11.3 - Organic solvents like benzene, ether, and...Ch. 11.4 - Prob. 8PCh. 11.4 - Prob. 9PCh. 11.4 - Prob. 10P
Ch. 11.5 - Rank the following substances in order of their...Ch. 11.5 - 3-Bromo-1-butene and 1-bromo-2-butene undergo SN1...Ch. 11.5 - Prob. 13PCh. 11.6 - Review the mechanism of geraniol biosynthesis...Ch. 11.7 - Prob. 15PCh. 11.7 - What alkyl halides might the following alkenes...Ch. 11.8 - Prob. 17PCh. 11.8 - Prob. 18PCh. 11.9 - Prob. 19PCh. 11.12 - Prob. 20PCh. 11.SE - Prob. 21VCCh. 11.SE - From what alkyl bromide was the following alkyl...Ch. 11.SE - Prob. 23VCCh. 11.SE - Prob. 24VCCh. 11.SE - Prob. 25MPCh. 11.SE - Prob. 26MPCh. 11.SE - Prob. 27MPCh. 11.SE - Prob. 28MPCh. 11.SE - Prob. 29MPCh. 11.SE - Prob. 30MPCh. 11.SE - Prob. 31MPCh. 11.SE - Prob. 32MPCh. 11.SE - Metabolism of S-adenosylhomocysteine (Section...Ch. 11.SE - Reaction of iodoethane with CN- yields a small...Ch. 11.SE - One step in the urea cycle for ridding the body of...Ch. 11.SE - Prob. 36MPCh. 11.SE - Prob. 37MPCh. 11.SE - Propose a mechanism for the following reaction, an...Ch. 11.SE - Prob. 39APCh. 11.SE - The following Walden cycle has been carried out....Ch. 11.SE - Prob. 41APCh. 11.SE - Which reactant in each of the following pairs is...Ch. 11.SE - Prob. 43APCh. 11.SE - Prob. 44APCh. 11.SE - Prob. 45APCh. 11.SE - Prob. 46APCh. 11.SE - Prob. 47APCh. 11.SE - Prob. 48APCh. 11.SE - Propose structures for compounds that fit the...Ch. 11.SE - What products would you expect from the reaction...Ch. 11.SE - Prob. 51APCh. 11.SE - Prob. 52APCh. 11.SE - Prob. 53APCh. 11.SE - Prob. 54APCh. 11.SE - Prob. 55APCh. 11.SE - Order each of the following sets of compounds with...Ch. 11.SE - Order each of the following sets of compounds with...Ch. 11.SE - Prob. 58APCh. 11.SE - Prob. 59APCh. 11.SE - Ethers can often be prepared by SN2 reaction of...Ch. 11.SE - Show the stereochemistry of the epoxide (see...Ch. 11.SE - Prob. 62APCh. 11.SE - In addition to not undergoing substitution...Ch. 11.SE - The tosylate of (2R, 3S)-3-phenyl-2-butanol...Ch. 11.SE - Prob. 65APCh. 11.SE - Prob. 66APCh. 11.SE - Prob. 67APCh. 11.SE - Prob. 68APCh. 11.SE - Prob. 69APCh. 11.SE - (S)-2-Butanol slowly racemizes on standing in...Ch. 11.SE - Reaction of HBr with (R)-3-methyl-3-hexanol leads...Ch. 11.SE - Treatment of 1-bromo-2-deuterio-2-phenylethane...Ch. 11.SE - Prob. 73APCh. 11.SE - Prob. 74APCh. 11.SE - In light of your answer to Problem 11-74, explain...Ch. 11.SE - Prob. 76APCh. 11.SE - Compound X is optically inactive and has the...Ch. 11.SE - When a primary alcohol is treated with...Ch. 11.SE - Prob. 79APCh. 11.SE - Amines are converted into alkenes by a two-step...Ch. 11.SE - The antipsychotic drug flupentixol is prepared by...
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- The following questions ask you to choose which of the pair reactions shown has been correctly identified as faster. Choose all correct answers with explanation In the SN2 displacement by iodide of CH3Cl or of CH3OTs, CH3OTs reacts faster. In the SN2 displacement by acetate of bromoethane or bromocyclohexane, bromocyclohexane reacts faster. In the SN2 displacement by CH3CH2O- or by CN- on 2-bromopropane, CN- reacts faster. n the SN2 displacement by HC≡C- on bromomethane in benzene or in acetonitrile, reaction in benzene goes faster.arrow_forwardExplain how the reaction of (CH3)2CHCH(Cl)CH3 with H2O yields two substitutionproducts, (CH3)2CHCH(OH)CH3 and (CH3)2C(OH)CH2CH3arrow_forwardDraw the four resonance structures formed during bromination of methoxybenzene, CH3OC6H5, with Br2/FeBr3 to give para-bromomethoxybenzene and then circle the most stable resonance form.arrow_forward
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