Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 7, Problem 7.87P
In some nucleophilic substitutions under
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The bicyclic heterocycles quinoline and indole undergo electrophilic aromatic substitution to give the products shown. (a) Explain why electrophilic substitution occurs on the ring without the N atom for quinoline, but occurs on the ring with the N atom in indole. (b) Explain why electrophilic substitution occurs more readily at C8 than C7 in quinoline. (c) Explain whyelectrophilic substitution occurs more readily at C3 rather than C2 of indole.
H
9. (a) Optically active 2-bromobutane undergoes racemization on treatment with
a solution of KBr. Give a mechanism for this racemization.
(b) In contrast, optically active butan-2-ol does not racemize on treatment with
a solution of KOH. Explain why a reaction like that in part (a) does not occur.
(c) Optically active butan-2-ol racemizes in dilute acid. Propose a mechanism
for this racemization.
(a) Draw all stereoisomers formed by monochlorination of the cis and trans isomers of 1,2-dimethylcyclobutane drawn below. (b) How many constitutional isomers are formed in each reaction? (c) Label any pairs of enantiomers formed.
Chapter 7 Solutions
Organic Chemistry
Ch. 7 - Classify each alkyl halide as 1 , 2, or 3.Ch. 7 - Problem 7.1 Telfairine, a naturally occurring...Ch. 7 - Draw the structure of an alkyl bromide with...Ch. 7 - Give the IUPAC name for each compound. a. b. c. d.Ch. 7 - Prob. 7.5PCh. 7 - An sp3 hybridized CCl bond is more polar than an...Ch. 7 - Prob. 7.7PCh. 7 - Problem 7.6 Identify the nucleophile and leaving...Ch. 7 - Prob. 7.9PCh. 7 - Prob. 7.10P
Ch. 7 - Prob. 7.11PCh. 7 - Prob. 7.12PCh. 7 - Does the equilibrium favor the reactants or...Ch. 7 - Prob. 7.14PCh. 7 - Prob. 7.15PCh. 7 - Classify each solvent as protic or aprotic. a. b....Ch. 7 - Prob. 7.17PCh. 7 - Prob. 7.18PCh. 7 - Prob. 7.19PCh. 7 - Prob. 7.20PCh. 7 - Prob. 7.21PCh. 7 - Draw an energy diagram for the reaction in Problem...Ch. 7 - Draw the product of each SN2 reaction and indicate...Ch. 7 - Prob. 7.24PCh. 7 - Prob. 7.25PCh. 7 - What happens to the rate of an SN1 reaction under...Ch. 7 - Draw the products of each SN1 reaction and...Ch. 7 - Classify each carbocation as 1,2, or 3. a. b. c....Ch. 7 - Prob. 7.29PCh. 7 - Prob. 7.30PCh. 7 - Which alkyl halide in each pair reacts faster in...Ch. 7 - Prob. 7.32PCh. 7 - Problem 7.30 For each alkyl halide and...Ch. 7 - Prob. 7.34PCh. 7 - Prob. 7.35PCh. 7 - Prob. 7.36PCh. 7 - Prob. 7.37PCh. 7 - Prob. 7.38PCh. 7 - Prob. 7.39PCh. 7 - Prob. 7.40PCh. 7 - Prob. 7.41PCh. 7 - Give the IUPAC name for each compound, including...Ch. 7 - Draw the products formed when each alkyl halide is...Ch. 7 - Give the IUPAC name for each compound. a. c....Ch. 7 - Prob. 7.45PCh. 7 - Classify each alkyl halide in Problem 7.44 as 1 ,...Ch. 7 - Draw the eight constitutional isomers having the...Ch. 7 - Prob. 7.48PCh. 7 - Draw the substitution product that results when...Ch. 7 - Draw the products of each nucleophilic...Ch. 7 - Prob. 7.51PCh. 7 - Rank the species in each group in order of...Ch. 7 - Which of the following nucleophilic substitution...Ch. 7 - Prob. 7.54PCh. 7 - Prob. 7.55PCh. 7 - Prob. 7.56PCh. 7 - 7.53 Consider the following reaction.
Draw a...Ch. 7 - Prob. 7.58PCh. 7 - Prob. 7.59PCh. 7 - Draw the products of each SN2 reaction and...Ch. 7 - Prob. 7.61PCh. 7 - Prob. 7.62PCh. 7 - Prob. 7.63PCh. 7 - Consider the following SN1 reaction. a.Draw a...Ch. 7 - Prob. 7.65PCh. 7 - Prob. 7.66PCh. 7 - Draw the products of each SN1 reaction and...Ch. 7 - Prob. 7.68PCh. 7 - Prob. 7.69PCh. 7 - Diphenhydramine, the antihistamine in Benadryl,...Ch. 7 - Draw a stepwise, detailed mechanism for the...Ch. 7 - When a single compound contains both a nucleophile...Ch. 7 - Prob. 7.73PCh. 7 - Prob. 7.74PCh. 7 - Draw a stepwise, detailed mechanism f or the...Ch. 7 - Prob. 7.76PCh. 7 - Fill in the appropriate reagent or starting...Ch. 7 - Devise a synthesis of each compound from an alkyl...Ch. 7 - Prob. 7.79PCh. 7 - Suppose you have compounds A-D at y our disposal....Ch. 7 - Prob. 7.81PCh. 7 - Prob. 7.82PCh. 7 - Prob. 7.83PCh. 7 - Prob. 7.84PCh. 7 - 7.80 As we will learn in Chapter 9, an epoxide is...Ch. 7 - Prob. 7.86PCh. 7 - In some nucleophilic substitutions under SN1...
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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- The bicyclic heterocycles quinoline and indole undergo electrophilic aromatic substitution to give the products shown. (a) Explain why electrophilic substitution occurs on the ring without the N atom for quinoline, but occurs on the ring with the N atom in indole. (b) Explain why electrophilic substitution occurs more readily at C8 than C7 in quinoline. (c) Explain why electrophilic substitution occurs more readily at C3 rather than C2 of indole.arrow_forwardThe reaction of butan-2-ol with concentrated aqueous HBr goes with partial racemization, giving more inversion thanretention of configuration. Propose a mechanism that accounts for racemization with excess inversion.(b) Under the same conditions, an optically active sample of trans-2-bromocyclopentanol reacts with concentrated aqueous HBr to give an optically inactive product, (racemic) trans-1,2-dibromocyclopentane. Proposea mechanism to show how this reaction goes with apparently complete retention of configuration, yet withracemization. (Hint: Draw out the mechanism of the reaction of cyclopentene with Br2 in water to give thestarting material, trans-2- bromocyclopentanol. Consider how parts of this mechanism might be involved in thereaction with HBr.)arrow_forward(a) What alkene yields A and B when it is treated with Br2 in CCl4? (b) What alkene yields C and D under the same conditions?arrow_forward
- Dehydration of 1,2,2-trimethylcyclohexanol with H2SO4 affords 1-tertbutylcyclopentene as a minor product. (a) Draw a stepwise mechanism that shows how this alkene is formed. (b) Draw other alkenes formed in this dehydration. At least one must contain a five-membered ring.arrow_forwardWhen (R)-6-bromo-2,6-dimethylnonane is dissolved in CH3OH, nucleophilic substitution yields an optically inactive solution. When the isomeric halide (R)-2-bromo-2,5-dimethylnonane is dissolved in CH3OH under the same conditions, nucleophilic substitution forms an optically active solution. Draw the products formed in each reaction, and explain why the difference in optical activity is observed.arrow_forwardDehydration of 1,2,2-trimethylcyclohexanol with H2SO4 affords 1-tert-butylcyclopentene as a minor product. (a) Draw a stepwise mechanism that shows how this alkene is formed. (b) Draw other alkenes formed in this dehydration. At least one must contain a five-membered ring.arrow_forward
- Consider the tetracyclic compound with rings labeled A–D. (a) Which ring is the most reactive in electrophilic aromatic substitution? (b) Which ring is the least reactive in electrophilic aromatic substitution?arrow_forwardQ3. 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? Q4 Which statement below about Sn1 reactions is incorrect? (A) SN1 reactions are stepwise and have intermediates. (B) The slow step in a SN1 reaction is formation of the carbocation intermediate. (C) SN1 reactions have first order kinetics which means only the alkyl halide is involved in the rate limiting step. (D) The products of a SN1 reaction will be a pair of enantiomers. (E) An aprotic solvent is best for Sn1 reactions as they tend to help stabilize carbocation intermediates.arrow_forwardWhen (ft)-6-bromo-2,6-dimethylnonane is dissolved in CH3OH, nucleophilic substitution yields an optically inactive solution. When the isomeric halide (fl)-2-bromo-2,5- dimethylnonane is dissolved in CH3OH under the same conditions, nucleophilic substitution forms an optically active solution. Draw the products formed in each reaction, and explain why the difference in optical activity is observed.arrow_forward
- The alkyl halide cis-1-bromo-4-methycyclohexane (A) undergoes a (c) substitution reaction when treated with H,0 to give a racemic mixture which is made up of product B and C. (i) What is a racemic mixture? (ii) Draw all the possible diastereoisomers of the compound below. Br Brarrow_forwardConsider the tetracyclic aromatic compound drawn below, with rings labeled as A, B, C, and D. (a) Which of the four rings is most reactive in electrophilic aromatic substitution? (b) Which of the four rings is least reactive in electrophilic aromatic substitution? (c) What are the major product(s) formed when this compound is treated with one equivalent of Br2?arrow_forwardWhen tert-butyl bromide is heated with an equal amount of ethanol in an inert solvent, one of the products is ethyl tert-butyl ether. (a) What happens to the reaction rate if the concentration of ethanol is doubled?arrow_forward
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