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Ch.10 - Structure and Synthesis of Alcohols
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook
All textbooksWade 9th EditionCh.10 - Structure and Synthesis of AlcoholsProblem 38a
Chapter 10, Problem 38a

Show how you would synthesize the following alcohol from appropriate alkene.
(a)

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Identify the target alcohol: The structure provided is 2-butanol, which has a hydroxyl (-OH) group attached to the second carbon of a butane chain.
Determine the appropriate alkene precursor: To synthesize 2-butanol, the corresponding alkene would be 2-butene, as the hydroxyl group will be added to the second carbon during the reaction.
Choose the reaction mechanism: The synthesis of an alcohol from an alkene can be achieved through hydration. Specifically, acid-catalyzed hydration or oxymercuration-demercuration can be used to add water (H₂O) across the double bond of the alkene.
Explain regioselectivity: In this case, Markovnikov's rule applies, meaning the hydroxyl group will attach to the more substituted carbon (the second carbon in 2-butene) during the reaction.
Outline the procedure: For acid-catalyzed hydration, treat 2-butene with dilute sulfuric acid (H₂SO₄) and water. Alternatively, for oxymercuration-demercuration, react 2-butene with mercuric acetate (Hg(OAc)₂) in water, followed by reduction with sodium borohydride (NaBH₄). Both methods will yield 2-butanol.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Alkene Reactivity

Alkenes are unsaturated hydrocarbons characterized by at least one carbon-carbon double bond. Their reactivity is primarily due to this double bond, which can undergo various reactions such as electrophilic addition. Understanding how alkenes react is crucial for synthesizing alcohols, as the addition of water (hydration) to an alkene can yield an alcohol.
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Hydration Reaction

Hydration is a chemical reaction where water is added to a compound. In organic chemistry, the hydration of alkenes typically involves the addition of water across the double bond, often in the presence of an acid catalyst. This process converts the alkene into an alcohol, making it essential for synthesizing alcohols from alkenes.
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Markovnikov's Rule

Markovnikov's Rule states that when HX (where X is a halogen or OH) is added to an asymmetric alkene, the hydrogen atom will attach to the carbon with the greater number of hydrogen atoms already attached. This principle is important in predicting the outcome of hydration reactions, as it helps determine the structure of the resulting alcohol based on the alkene's substitution pattern.
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Related Practice
Textbook Question

Starting from bromobenzene and any other reagents and solvents you need, show how you would synthesize the following compounds. Any of these products may be used as starting materials in subsequent parts of this problem.

c. 1-phenylpropan-2-ol

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Textbook Question

Show how you would use Grignard syntheses to prepare the following alcohol from the indicated starting material and any other necessary reagents.

(a) octan-3-ol from hexanal, CH3(CH2)4CHO

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Textbook Question

Show how you would synthesize the following alcohol from appropriate alkene.

(d)

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Textbook Question

Show how you would synthesize the following alcohol from appropriate alkene.

(b)

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Textbook Question

Write structures for a homologous series of alcohols (R―OH) having from one to six carbons.

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Textbook Question

Starting from bromobenzene and any other reagents and solvents you need, show how you would synthesize the following compounds. Any of these products may be used as starting materials in subsequent parts of this problem.

d. 3-phenylprop-2-en-1-ol

757
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