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Ch. 9 - Alkenes 2: Oxidation and Reduction
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471당신이 사용하는 게 아니라요?교과서 변경
모든 교과서Mullins 1st EditionCh. 9 - Alkenes 2: Oxidation and Reduction문제 30b
8장, 문제 30b

Suggest a synthesis of the following aldehydes or ketones using the ozonolysis reaction of an alkene.
(b) Ozonolysis reaction of an alkene forming benzaldehyde and acetaldehyde using ozone and dimethyl sulfide.

검증된 단계별 안내
1
Identify the products of the ozonolysis reaction: acetophenone (C₆H₅C(O)CH₃) and formaldehyde (HCHO).
Recognize that ozonolysis cleaves the double bond of an alkene to form carbonyl compounds. The products suggest the original alkene had a structure that splits into these two fragments.
Determine the structure of the alkene that would yield acetophenone and formaldehyde upon ozonolysis. The alkene must have a double bond between the carbon atoms that will form the carbonyl groups in the products.
Consider the connectivity of the alkene: the carbon atom that forms acetophenone must be connected to the phenyl group and a methyl group, while the carbon atom that forms formaldehyde must be connected to a hydrogen atom.
Propose the structure of the alkene: phenylpropene (C₆H₅CH=CH₂), where the double bond is between the terminal carbon and the adjacent carbon, allowing for the formation of acetophenone and formaldehyde upon ozonolysis.

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이 영상 해법은 위 문제에 도움이 된다고 튜터들이 추천한 것입니다.

주요 개념

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

Ozonolysis Reaction

Ozonolysis is a reaction where ozone (O3) cleaves alkenes to form carbonyl compounds, such as aldehydes and ketones. The reaction involves the formation of an ozonide intermediate, which is then reduced to yield the final products. This process is useful for determining the position of double bonds in alkenes and synthesizing specific carbonyl compounds.
추천 영상:
06:30
General properties of ozonolysis.

Alkene Structure

The structure of the alkene is crucial in ozonolysis as it determines the resulting carbonyl compounds. In the given image, the alkene must have a double bond positioned such that upon cleavage, it forms the specified ketone and aldehyde. Understanding the connectivity and substitution pattern of the alkene helps predict the ozonolysis products accurately.
추천 영상:
가이드 코스
1:59
Alkene Metathesis Concept 5

Reductive Workup

Reductive workup in ozonolysis involves using a reducing agent, such as dimethyl sulfide (CH3SCH3), to convert the ozonide intermediate into stable carbonyl compounds. This step is essential to prevent the formation of unwanted by-products and ensure the desired aldehydes and ketones are obtained. The choice of reducing agent can influence the yield and purity of the final products.
추천 영상:
03:16
Reductive Workup Mechanism:
관련 실천
교과서 질문

Draw the product(s) you'd expect when each of these alkenes is treated first with O3, then with CH3SCH3

(c)

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교과서 질문

Draw the product(s) you'd expect when each of these alkenes is treated first with O3, then with CH3SCH3

(d)

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교과서 질문

Formation of the molozonide can be expected to proceed stereospecifically. Why is this the case? Show the two different molozonides you would expect to get from ozonolysis of (E)- and (Z)-3,4-dimethylhept-3-ene.


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교과서 질문

Suggest a synthesis of the following aldehydes or ketones using the ozonolysis reaction of an alkene.

(a)

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교과서 질문

What product results when the following molecules are treated with H₂ Pd/C? Be sure to indicate the relative stereochemical outcome. Draw both enantiomers of any racemic mixtures. [It is difficult to control the stoichiometry of gases so there is enough H₂ to reduce all alkenes.]

(b)

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교과서 질문

In Solved Assessment 9.30(b), we came up with an alkene that under the conditions of ozonolysis would produce acetophenone and acetaldehyde. There is one other alkene that should produce the same compounds under these conditions. Which is it?

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