Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives

Bruice8th EditionOrganic ChemistryISBN: 9780135213711당신이 사용하는 게 아니라요?교과서 변경

Bruice 8th Edition

Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives

문제 24

16장, 문제 24

What are the products of the following reactions?
a.
b.
c.
d.

검증된 단계별 안내

Step 1: Understand the role of H2 and Raney Ni in these reactions. Raney nickel (Ni) is a catalyst commonly used for hydrogenation reactions. It facilitates the addition of hydrogen (H2) to unsaturated bonds such as double bonds, triple bonds, nitriles, and carbonyl groups.

Step 2: For reaction (a), identify the functional group in the starting material. If the starting material contains a double or triple bond, Raney Ni will catalyze the hydrogenation, converting it to a single bond. For example, an alkene (C=C) will be reduced to an alkane (C-C).

Step 3: For reaction (b), CH3CH2CH2C≡N, recognize that the nitrile group (C≡N) undergoes hydrogenation in the presence of H2 and Raney Ni. This reaction converts the nitrile group into a primary amine (-CH2NH2).

Step 4: For reaction (c), analyze the starting material. If it contains a functional group such as a carbonyl (C=O) or an unsaturated bond, Raney Ni will catalyze its reduction. For example, a ketone (C=O) will be reduced to an alcohol (-CH2OH).

Step 5: For reaction (d), CH3(C=O)OCH3, identify the ester functional group. Under hydrogenation conditions with Raney Ni, the ester can be reduced to an alcohol. Specifically, the ester bond (C=O and C-O) will break, forming two alcohols: one from the carbonyl group and one from the alkoxy group.

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주요 개념

질문에 올바르게 답하기 위해 반드시 이해해야 하는 핵심 개념들은 다음과 같습니다.

Hydrogenation

Hydrogenation is a chemical reaction that involves the addition of hydrogen (H2) to unsaturated organic compounds, typically alkenes or alkynes, to convert them into saturated hydrocarbons. This process is often facilitated by catalysts such as Raney nickel, which enhances the reaction rate and selectivity. Understanding hydrogenation is crucial for predicting the products of reactions involving unsaturated substrates.

Raney Nickel Catalyst

Raney nickel is a finely divided nickel-aluminum alloy that serves as a highly effective catalyst for hydrogenation reactions. It is particularly useful in reducing carbon-carbon double and triple bonds, as well as in the hydrogenation of functional groups like nitriles and carbonyls. Familiarity with the properties and applications of Raney nickel is essential for understanding its role in the reactions presented.

Functional Group Transformations

Functional group transformations refer to the chemical reactions that convert one functional group into another, altering the reactivity and properties of organic molecules. In the context of the given reactions, recognizing how hydrogenation affects various functional groups, such as nitriles and esters, is vital for predicting the final products. This concept is foundational in organic synthesis and reaction mechanisms.

What are the products of the following reactions?a. b. c. d.