Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 7.12, Problem 19P
Interpretation Introduction
Interpretation:
Thestructural formula for the carbocation intermediate formed in the dehydration of each of the alcohols is to be written. By using Curved arrows the way in which carbocation is deprotonated by water to give a mixture of
Concept introduction:
>The dehydration of alcohol results in the loss of
The
The dehydration of primary alcohols proceeds through
The dehydration of secondary and tertiary alcohols proceeds through
The
The carbocation is formed at the carbon where the hydroxyl group is attached.
>The secondary and tertiary alcohols can produce more than one product if the hydroxyl-bearing carbon has nonequivalent adjacent carbons.
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. Each of the following alcohols or alkyl halides has been subjected to either acid-catalyzed dehydration or base dehydrohalogenation respectively and yields a mixture of two or more isomeric alkenes. Identify the alkenes in each case, and predict which one is the major product on the basis of either Zaitsev rule, stability of the alkene or rearrangement. Give the IUPAC name, including stereochemistry where necessary, of each organic reactant and product and state whether it is the E1 or E2 product
Arrange the alkenes in each set in order of increasing rate of reaction with HI and
explain the basis for your ranking. Draw the structural formula of the major product
formed in each case.
(a)
and
(b) H3CH₂CHC=CH₂ and (H3C) 2C=CHCH3
7.55
Acid-catalyzed dehydration of 2,2-dimethyl-1-hexanol gave a number of isomeric alkenes including 2-
methyl-2-heptene as shown in the following equation.
H2SO4
НО
heat
(a) Write a stepwise mechanism for the formation of 2-methyl-2-heptene, using curved arrows to show the
flow of electrons.
(b) What other alkenes do you think are formed in this reaction?
Chapter 7 Solutions
Organic Chemistry - Standalone book
Ch. 7.1 - Name each of the following using IUPAC...Ch. 7.1 - Prob. 2PCh. 7.2 - How many carbon atoms are sp2-hybridized in the...Ch. 7.3 - Prob. 4PCh. 7.3 - Are cis-2-hexene and trans-3-hexene stereoisomers?...Ch. 7.4 - Prob. 6PCh. 7.4 - Prob. 7PCh. 7.4 - Give the IUPAC name of each of the compounds in...Ch. 7.5 - Arrange the following in order of increasing...Ch. 7.6 - Prob. 10P
Ch. 7.6 - Standard enthalpies of formation are known for all...Ch. 7.6 - Prob. 12PCh. 7.6 - Despite numerous attempts, the alkene...Ch. 7.6 - Write structural formulas for the six isomeric...Ch. 7.7 - Place a double bond in the carbon skeleton shown...Ch. 7.9 - Identify the alkene obtained on dehydration of...Ch. 7.10 - Prob. 17PCh. 7.11 - Prob. 18PCh. 7.12 - Prob. 19PCh. 7.13 - The alkene mixture obtained on dehydration of...Ch. 7.14 - Write the structures of all the alkenes that can...Ch. 7.14 - Write structural formulas for all the alkenes that...Ch. 7.15 - A study of the hydrolysis behavior of...Ch. 7.15 - Use curved arrows to illustrate the electron flow...Ch. 7.15 - Predict the major product of the reaction shown.Ch. 7.16 - Prob. 26PCh. 7.17 - Prob. 27PCh. 7.18 - Prob. 28PCh. 7.19 - Predict the major organic product of each of the...Ch. 7.19 - A standard method for the synthesis of ethers is...Ch. 7 - Write structural formulas for each of the...Ch. 7 - Prob. 32PCh. 7 - Give an IUPAC name for each of the following...Ch. 7 - A hydrocarbon isolated from fish oil and from...Ch. 7 - Prob. 35PCh. 7 - Prob. 36PCh. 7 - Prob. 37PCh. 7 - Prob. 38PCh. 7 - Choose the more stable alkene in each of the...Ch. 7 - Suggest an explanation for the fact that...Ch. 7 - Prob. 41PCh. 7 - Write structural formulas for all the alkene...Ch. 7 - Prob. 43PCh. 7 - Prob. 44PCh. 7 - Predict the major organic product of each of the...Ch. 7 - Prob. 46PCh. 7 - Prob. 47PCh. 7 - The rate of the reaction In the first order in...Ch. 7 - Prob. 49PCh. 7 - Prob. 50PCh. 7 - You have available 2,2-dimethylcyclopentanol (A)...Ch. 7 - Prob. 52PCh. 7 - Prob. 53PCh. 7 - Prob. 54PCh. 7 - Acid-catalyzed dehydration of...Ch. 7 - The ratio of elimination to substitution is...Ch. 7 - Prob. 57PCh. 7 - Prob. 58DSPCh. 7 - Prob. 59DSPCh. 7 - Prob. 60DSPCh. 7 - Prob. 61DSPCh. 7 - A Mechanistic Preview of Addition Reactions The...Ch. 7 - Prob. 63DSPCh. 7 - Prob. 64DSPCh. 7 - Prob. 65DSP
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