Introduction to General, Organic and Biochemistry
12th Edition
ISBN: 9780357391594
Author: Frederick A. Bettelheim; William H. Brown; Mary K. Campbell
Publisher: Cengage Learning US
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Chapter 13, Problem 65P
Interpretation Introduction
Interpretation: The step-by-step equation and complete mechanism needs to be shown for the given
Concept Introduction: According to the question, the mechanism for the acid-catalyzed hydration is same as the acid-catalyzed by hydration of an
Step 1: Addition of proton.
Step 2: Formation of new covalent bond between an electrophile and a nucleophile.
Step 3: Removal of proton.
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Students have asked these similar questions
Hydration of aldehydes and ketones can be catalyzed by acid
or base. Bases catalyze hydration by:
protonating the carbonyl oxygen
making the carbonyl group more electrophilic
employing hydroxide ion, which is a better nucleophile than water
making the carbonyl group less electrophilic
shifting the equilibrium position of the reaction to favor products
help
Alcohols are acidic in nature. Therefore, a strong base can
abstract the acidic hydrogen atom of the alcohol in a process
known as deprotonation. The alcohol forms an alkoxide ion by
losing the proton attached to the oxygen atom of the hydroxyl (
-OH) group. The alkoxide formed can act as a base or a
nucleophile depending on the substrate and reaction conditions.
However, not all bases can abstract the acidic proton of alcohols
and not all alcohols easily lose the proton. Deprotonation
depends on the strength of the base and the acidity of the
alcohol. Strong bases, such as NaNH2, can easily abstract a
proton from almost all alcohols. Likewise, more acidic alcohols
lose a proton more easily.
Determine which of the following reactions would undergo deprotonation based on the strength of the base and the acidity of the alcohol.
Check all that apply.
► View Available Hint(s)
CH3CH,OH + NH3 →CH,CH,O-NH
CH3
CH3
H3C-C-H+NH3 → H3 C-C-H
OH
O-NH
CH3CH2OH + NaNH, → CH3CH,O-Na* + NH3
CHC12
Cl₂…
Chapter 13 Solutions
Introduction to General, Organic and Biochemistry
Ch. 13.1 - Prob. 13.1QCCh. 13.1 - Prob. 13.2QCCh. 13.2 - Problem 14-3 Draw structural formulas for the...Ch. 13.2 - Prob. 13.4QCCh. 13.2 - Prob. 13.5QCCh. 13.3 - Problem 14-6 Write the common name for each ether.Ch. 13.4 - Prob. 13.7QCCh. 13.4 - Prob. 13.8QCCh. 13 - 14-8 Answer true or false. The functional group of...Ch. 13 - 14-9 What is the difference in structure between a...
Ch. 13 - 14-10 Which of the following are secondary...Ch. 13 - 14-11 Which of the alcohols in Problem 14-10 are...Ch. 13 - 14-12 Write the 1UPAC name of each compound. (e)...Ch. 13 - Prob. 6PCh. 13 - Prob. 7PCh. 13 - 14-15 Both alcohols and phenols contain an —OH...Ch. 13 - Prob. 9PCh. 13 - 14-17 Explain in terms of noncovalent interactions...Ch. 13 - Prob. 11PCh. 13 - Prob. 12PCh. 13 - 14-20 Show hydrogen bonding between methanol and...Ch. 13 - 14-21 Show hydrogen bonding between the oxygen of...Ch. 13 - 14-22 Arrange these compounds in order of...Ch. 13 - 14-23 Arrange these compounds in order of...Ch. 13 - 14-24 2-Propanol (isopropyl alcohol) is commonly...Ch. 13 - Prob. 18PCh. 13 - Prob. 19PCh. 13 - Prob. 20PCh. 13 - 14-28 Give the structural formula of an alkene or...Ch. 13 - Prob. 22PCh. 13 - 14-30 Show how to distinguish between cyclohexanol...Ch. 13 - 14-31 Compare the acidity of alcohols and phenols,...Ch. 13 - 14-32 Both 2,6-diisopropylcyclohexanol and the...Ch. 13 - 14-33 Write equations for the reaction of...Ch. 13 - 14-34 Write equations for the reaction of...Ch. 13 - 14-35 Write equations for the reaction of each of...Ch. 13 - 14-36 Show how to convert cyclohexanol to these...Ch. 13 - Prob. 30PCh. 13 - Prob. 31PCh. 13 - 14-39 Name two important alcohols derived from...Ch. 13 - 14-40 Name two important alcohols derived from...Ch. 13 - Prob. 34PCh. 13 - 14-42 Write the common name for each ether. ch3...Ch. 13 - Prob. 36PCh. 13 - 14-44 Answer true or false. (a) The functional...Ch. 13 - Prob. 38PCh. 13 - Write the common name for each thiol in Problem 38...Ch. 13 - 14-47 Following are structural formulas for...Ch. 13 - 14-48 Explain why methanethiol, CH3SH, has a lower...Ch. 13 - 14-49 Answer true or false. Today, the major...Ch. 13 - (Chemical Connections 13A ) As stated in the...Ch. 13 - Prob. 44PCh. 13 - Prob. 45PCh. 13 - Prob. 46PCh. 13 - Prob. 47PCh. 13 - (Chemical Connections 13D ) Show that enflurane...Ch. 13 - Prob. 49PCh. 13 - 14-60 Write a balanced equation for the complete...Ch. 13 - 14-61 Knowing what you do about electronegativity,...Ch. 13 - 14-62 Draw structural formulas and write IUPAC...Ch. 13 - Prob. 53PCh. 13 - 14-64 Explain why the boiling point of ethylene...Ch. 13 - Prob. 55PCh. 13 - 14-66 1,4-Butanediol, hexane, and 1-pentanol have...Ch. 13 - 14-67 Of the three compounds given in Problem...Ch. 13 - Prob. 58PCh. 13 - 14-69 Show how to prepare each compound from...Ch. 13 - 14-70 Show how to prepare each compound from...Ch. 13 - 14-71 The mechanism of the acid-catalyzed...Ch. 13 - Prob. 62PCh. 13 - 14-73 Lipoic acid is a growth factor for many...Ch. 13 - 14-74 Following is a structural formula for the...Ch. 13 - Prob. 65PCh. 13 - Prob. 66PCh. 13 - Prob. 67PCh. 13 - 14-78 Consider alkenes A, B, and C. each of which...Ch. 13 - Prob. 69P
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- When propene reacts with gaseous hydrogen bromide, HBr, two products, 1-bromopropane and 2-bromopropane are formed. The reaction is a two-step process in which the electrophilic attack occurs in the first step. Identify the electrophile in this reaction Draw a diagram showing the first step of the reaction that leads to the production of 2-bromopropane.arrow_forwardThe addition of water to aldehydes and ketones occurs rapidly, although it is not thermodynamically favored. What would be the product for the reaction above? Hint: Think of the self-ionization of water and the polarity of the carbonyl group.arrow_forwardWhen trans-2-chloro-1-cyclohexanol is treated with a base, cyclohexene oxide is the product. However, when cis-2-chloro-1-cyclohexanol is treated with a base, the product is cyclohexanone. Write the mechanism for each of the two reactions.arrow_forward
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