For each reaction, give the expected substitution product and predict whether the mechanism will be first order (SN1) or second order (SN2): a) 2-chloro-2-methylbutane + CH3COOH b) isobutyl bromide + NaOMe c) 1-iodo-1-methylcyclohexane + CH3CH2OH Q3. 2-Bromopentane, when treated with ‎ alcoholic KOH yields a mixture of three alkenes A, B and C. Identify A, B and C. Which is predominant?

For each reaction, give the expected substitution product and predict whether the mechanism will be first order (SN1) or second order (SN2): a) 2-chloro-2-methylbutane + CH3COOH b) isobutyl bromide + NaOMe c) 1-iodo-1-methylcyclohexane + CH3CH2OH Q3. 2-Bromopentane, when treated with ‎ alcoholic KOH yields a mixture of three alkenes A, B and C. Identify A, B and C. Which is predominant?

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter18: Functional Derivatives Of Carboxylic Acids

Section: Chapter Questions

Problem 18.38P: A step in a synthesis of PGE1 (prostaglandin E1, alprostadil) is the reaction of a trisubstituted...

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For each reaction, give the expected substitution product and predict whether the mechanism will be first order (SN1) or second order (SN2): a) 2-chloro-2-methylbutane + CH3COOH b) isobutyl bromide + NaOMe c) 1-iodo-1-methylcyclohexane + CH3CH2OH
for each reaction give the expected substitution product and predict wether the mechanism will be first order (SN1) or second order (SN2) a) 2-chloro-2-methylbutane + CH3COOH b) isobutyl bromide + NaOMe c) 1-iodo-methylcyclohexane + CH3CH2OH
Following are diastereomers (A) and (B) of 3-bromo-3,4-dimethylhexane. On treatment with sodium ethoxide in ethanol, each gives 3,4-dimethyl-3-hexene as the major product. One diastereomer gives the E alkene, and the other gives the Z alkene. Which diastereomer gives which alkene? Account for the stereoselectivity of each -elimination.
A step in a synthesis of PGE1 (prostaglandin E1, alprostadil) is the reaction of a trisubstituted cyclohexene with bromine to form a bromolactone. Propose a mechanism for formation of this bromolactone and account for the observed stereochemistry of each substituent on the cyclohexane ring. Alprostadil is used as a temporary therapy for infants born with congenital heart defects that restrict pulmonary blood flow. It brings about dilation of the ductus arteriosus, which in turn increases blood flow in the lungs and blood oxygenation.
Reaction of HBr with 2-methylpropene yields 2-bromo-2-methylpropane. What is the structure of the carbocation formed during the reaction? Show the mechanism of the reaction.
a)Write the SN2 reaction mechanism between iodobutane with sodium hydroxide, NaOH. b)Predict the products and show the SN1 reaction mechanism that occurs with 2-iodo-2- methylpropane in aqueous sodium hydroxide, NaOH.
Propose a mechanism for addition of HI to 1-methylcyclohexene to give 1-iodo1-methylcyclohexane. Which step in your mechanism is rate-determining?
Pure (S)-2-bromo-2-fluorobutane reacts with methoxide ion in methanol to give a mixture of (S)-2-fluoro-2-methoxybutane and three fluoroalkenes.(a) Use mechanisms to show which three fluoroalkenes are formed.(b) Propose a mechanism to show how (S)-2-bromo-2-fluorobutane reacts to give (S)-2-fluoro-2-methoxybutane. Has thisreaction gone with retention or inversion of configuration?
2. (a) Write the reaction equation of substitution reaction when 1-bromopropane reacts with(i) NaOH aqueous(ii) Excess NH3(iii) KCNb) Write the reaction mechanism for the reaction in a)(i).
The reaction of (S)-2-bromopentane with potassium cyanide to yield 2-methylpentanenitrile (2-cyanopentane) occurs via a nucleophilic substitution pathway. The reaction is 100% stereospecific. Please explain in complete words what this observation tells you about the mechanism of the reaction.
1. Predict the elimination products of the following reactions. When two alkenes are possible, predict which one will be the major product. Explain your answers, showing the degree of substitution of each double bond in the products. 2. Which of these reactions are likely to produce both elimination and substitution products? (a) 2-bromopentane +NaOCH3 (b) 3-bromo-3-methylpentane +NaOMe(Me= methyl, CH3) (c) 2-bromo-3-ethylpentane +NaOH (d) cis-1-bromo-2-methylcyclohexane +NaOEt (Et= ethyl, CH2CH3)
Treatment of 2-bromo-2-methylbutane with KOH in ethanol yields a mixture of two Alkenes products. What are their likely structures? Show its mechanism.