14-71 The mechanism of the acid-catalyzed dehydration of an alcohol to an alkene is the reverse of the acid- catalyzed hydration of an alkene. The dehydration mechanism occurs by the following three steps. Step 1: Add a proton. Step 2: Break a bond to form stable molecules or ions. Step 3: Take away a proton. These three steps are illustrated here by the dehydration of 2-butanol to give 2-butene. Use curved arrows to show the flow of electrons in each step; that is, show how each bond-making or bond-breaking step occurs. H I + Step 3: CH 3 —CH—CH—CH 3 CH 3 —CH=CH—CH 3 + H + 2-butene

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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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Introduction to General, Organic a...

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

Solutions

Chapter 14, Problem 14.71P
Textbook Problem

14-71 The mechanism of the acid-catalyzed dehydration of an alcohol to an alkene is the reverse of the acid- catalyzed hydration of an alkene. The dehydration mechanism occurs by the following three steps.

Step 1: Add a proton.

Step 2: Break a bond to form stable molecules or ions. Step 3: Take away a proton.

These three steps are illustrated here by the dehydration of 2-butanol to give 2-butene. Use curved arrows to show the flow of electrons in each step; that is, show how each bond-making or bond-breaking step occurs.

Chapter 14, Problem 14.71P, 14-71 The mechanism of the acid-catalyzed dehydration of an alcohol to an alkene is the reverse of

H

I +

Step 3: CH3—CH—CH—CH3

CH3—CH=CH—CH3 + H +

2-butene

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Chapter 14 Solutions

Introduction to General, Organic and Biochemistry
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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