Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 7, Problem 7.68P
Interpretation Introduction
Interpretation: A stepwise mechanism of the given reaction is to be drawn and an explanation corresponding to the statement that
Concept introduction: The replacement or substitution of one
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Determine a stepwise mechanism for the following reaction that illustrates why two substitution
products are formed. Explain why 1-bromohex-2-ene reacts rapidly with a weak nucleophile (CH3OH)
under Syl reaction conditions, even though it is a 1° alkyl halide.
1-bromohex-2-ene
Part 1:
Br
CH₂OH
The first step in the reaction proceeds according to which mechanism?
CH₂CH₂CH₂CH=CHCH₂ + CH₂OH
CH₂CH₂CH₂CH:
Part 2:
Br
CHCH₂
Draw the missing resonance contributor.
OCH3 +
CH3CH₂CH₂CH=CHCH₂
CH3CH₂CH₂CH=CH-CH₂ + Br
Br
OCH 3
H₂CH₂CH₂CH=CH₂
view structure
+
+ Br
HBr
X
Provide reagents and reaction conditions for each step
1. Which alkene is the major product of this dehydration?
HO
H2SO4
heat
А
В
C
D
Chapter 7 Solutions
Organic Chemistry-Package(Custom)
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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