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14-79 On acid-catalyzed hydration of alkenes A and C in the previous problem, each gives only one alcohol with the molecular formula C 6 H 1 4 O. Draw the struc tural formulas for five other alkenes with the molecular formula C f j H 1 2 , each of which will also give only one alcohol upon acid-catalyzed hydration.

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Introduction to General, Organic a...

11th Edition
Frederick A. Bettelheim + 4 others
Publisher: Cengage Learning
ISBN: 9781285869759

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Chapter
Section
BuyFindarrow_forward

Introduction to General, Organic a...

11th Edition
Frederick A. Bettelheim + 4 others
Publisher: Cengage Learning
ISBN: 9781285869759
Chapter 14, Problem 14.79P
Textbook Problem
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14-79 On acid-catalyzed hydration of alkenes A and C in the previous problem, each gives only one alcohol with the molecular formula C6H14O. Draw the struc tural formulas for five other alkenes with the molecular formula CfjH12, each of which will also give only one alcohol upon acid-catalyzed hydration.

Interpretation Introduction

Interpretation:

The structural formulas of five other alkenes with the molecular formula C6H12 giving only one alcohol on acid-catalyzed hydration should be determined.

Concept Introduction:

The acid catalyzed hydration of alkenes result in the formation of alcohols. In this reaction, the hydrogen ion from the acid reacts with the pi electrons of the double bond resulting formation of carbocation. This carbocation can reacts with the lone pair on oxygen atom resulting substitution of hydronium ion group on the carbon having positive charge. The HSO4 ion so formed then abstract one hydrogen atom resulting the formation of alcohol.

Explanation of Solution

The five other alkenes having molecular formula C6H12 that undergoes acid-catalyzed hydration to form alcohol are as follows:

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Chapter 14 Solutions

Introduction to General, Organic and Biochemistry
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Ch. 14 - 14-11 Which of the alcohols in Problem 14-10 are...Ch. 14 - 14-12 Write the 1UPAC name of each compound. (e)...Ch. 14 - 14-13 Draw a structural formula for each alcohol....Ch. 14 - 14-14 Draw a structural formula for each of the...Ch. 14 - 14-15 Both alcohols and phenols contain an —OH...Ch. 14 - Prob. 14.16PCh. 14 - 14-17 Explain in terms of noncovalent interactions...Ch. 14 - 14-18 Explain in terms of noncovalent interactions...Ch. 14 - 14-19 Why does the water solubility of...Ch. 14 - 14-20 Show hydrogen bonding between methanol and...Ch. 14 - 14-21 Show hydrogen bonding between the oxygen of...Ch. 14 - 14-22 Arrange these compounds in order of...Ch. 14 - 14-23 Arrange these compounds in order of...Ch. 14 - 14-24 2-Propanol (isopropyl alcohol) is commonly...Ch. 14 - 14-25 Explain why glycerol is much thicker (more...Ch. 14 - 14-26 From each pair, select the compound that is...Ch. 14 - 14-27 Arrange the compounds in each set in order...Ch. 14 - 14-28 Give the structural formula of an alkene or...Ch. 14 - 14-29 Answer true or false. The two most important...Ch. 14 - 14-30 Show how to distinguish between cyclohexanol...Ch. 14 - 14-31 Compare the acidity of alcohols and phenols,...Ch. 14 - 14-32 Both 2,6-diisopropylcyclohexanol and the...Ch. 14 - 14-33 Write equations for the reaction of...Ch. 14 - 14-34 Write equations for the reaction of...Ch. 14 - 14-35 Write equations for the reaction of each of...Ch. 14 - 14-36 Show how to convert cyclohexanol to these...Ch. 14 - Prob. 14.37PCh. 14 - 14-38 Show how to convert this alcohol to...Ch. 14 - 14-39 Name two important alcohols derived from...Ch. 14 - 14-40 Name two important alcohols derived from...Ch. 14 - 14-41 Answer true or false. Ethanol and dimethyl...Ch. 14 - 14-42 Write the common name for each ether. ch3...Ch. 14 - 14-43 Write the common name for each of the...Ch. 14 - 14-44 Answer true or false. (a) The functional...Ch. 14 - 14-45 Write the IUPAC name of each thiol. SH I (a)...Ch. 14 - 14-46 Write the common name for each thiol in...Ch. 14 - 14-47 Following are structural formulas for...Ch. 14 - 14-48 Explain why methanethiol, CH3SH, has a lower...Ch. 14 - 14-49 Answer true or false. Today, the major...Ch. 14 - 14-50 (Chemical Connections 14A) As stated in the...Ch. 14 - 14-51 (Chemical Connections 14B) When was...Ch. 14 - 14-52 (Chemical Connections 14B) What was Alfred...Ch. 14 - 14-53 (Chemical Connections 14B) What is the...Ch. 14 - 14-54 (Chemical Connections 14C) What is the color...Ch. 14 - 14-55 (Chemical Connections 140 The legal...Ch. 14 - 14-56 (Chemical Connections 14D) What does it mean...Ch. 14 - 14-57 (Chemical Connections 14E) What are the...Ch. 14 - 14-58 (Chemical Connections 14E) Show that...Ch. 14 - 14-59 (Chemical Connections 14E) Would you expect...Ch. 14 - 14-60 Write a balanced equation for the complete...Ch. 14 - 14-61 Knowing what you do about electronegativity,...Ch. 14 - 14-62 Draw structural formulas and write IUPAC...Ch. 14 - 14-63 Draw structural formulas and write common...Ch. 14 - 14-64 Explain why the boiling point of ethylene...Ch. 14 - Prob. 14.65PCh. 14 - 14-66 1,4-Butanediol, hexane, and 1-pentanol have...Ch. 14 - 14-67 Of the three compounds given in Problem...Ch. 14 - 14-68 Each of the following compounds is a common...Ch. 14 - 14-69 Show how to prepare each compound from...Ch. 14 - 14-70 Show how to prepare each compound from...Ch. 14 - 14-71 The mechanism of the acid-catalyzed...Ch. 14 - Prob. 14.72PCh. 14 - 14-73 Lipoic acid is a growth factor for many...Ch. 14 - 14-74 Following is a structural formula for the...Ch. 14 - 14-75 As we will see in Chapter 16, the carbonyl...Ch. 14 - 14-76 Draw the structural formula for the hydrate...Ch. 14 - 14-77 With the exception of the acid-catalyzed...Ch. 14 - 14-78 Consider alkenes A, B, and C. each of which...Ch. 14 - 14-79 On acid-catalyzed hydration of alkenes A and...

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