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Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728당신이 사용하는 게 아니라요?교과서 변경
모든 교과서Wade 9th EditionCh. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy문제 15a,b,c
15장, 문제 15a,b,c

What dienes and dienophiles would react to give the following Diels–Alder products?
(a)
(b)
(c)

검증된 단계별 안내
1
Step 1: Analyze the Diels–Alder product structure to identify the diene and dienophile components. The Diels–Alder reaction involves a conjugated diene reacting with a dienophile (an electron-deficient alkene or alkyne). Look for the cyclohexene ring in the product, which is characteristic of this reaction.
Step 2: For product (a), observe the cyclohexene ring with a ketone group (COCH₃) attached. The diene must have two conjugated double bonds, and the dienophile must contain a carbonyl group (C=O) to form this product. The diene is likely 1,3-cyclopentadiene, and the dienophile is methyl vinyl ketone (CH₂=CHCOCH₃).
Step 3: For product (b), observe the aromatic ring with a ketone group (COOCH₂CH₃) attached. The diene must have two conjugated double bonds, and the dienophile must contain an ester group (COOCH₂CH₃). The diene is likely 1,3-butadiene, and the dienophile is ethyl acrylate (CH₂=CHCOOCH₂CH₃).
Step 4: For product (c), observe the cyclohexene ring with a nitrile group (CN) attached. The diene must have two conjugated double bonds, and the dienophile must contain a nitrile group (C≡N). The diene is likely furan (a heterocyclic diene), and the dienophile is acrylonitrile (CH₂=CHCN).
Step 5: Verify the stereochemistry and regiochemistry of the products. The Diels–Alder reaction is stereospecific, meaning the stereochemistry of the diene and dienophile will influence the final product. Ensure that the substituents on the diene and dienophile align correctly to form the observed products.

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이 영상 해법은 위 문제에 도움이 된다고 튜터들이 추천한 것입니다.
영상 길이:
4m

주요 개념

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

Diels–Alder Reaction

The Diels–Alder reaction is a [4+2] cycloaddition reaction between a conjugated diene and a dienophile, resulting in the formation of a six-membered ring. This reaction is a key method in organic synthesis for constructing cyclic compounds and is characterized by its stereospecificity and regioselectivity, making it a powerful tool for chemists.
추천 영상:
04:02
Diels-Alder Retrosynthesis

Dienes

Dienes are organic compounds that contain two double bonds. They can be classified as conjugated, where the double bonds are separated by a single bond, or isolated, where the double bonds are separated by more than one single bond. Conjugated dienes are particularly important in Diels–Alder reactions due to their ability to stabilize the transition state and facilitate the cycloaddition process.
추천 영상:
04:43
Drawing MO Diagram for Dienes

Dienophiles

Dienophiles are compounds that contain a double or triple bond and can react with dienes in the Diels–Alder reaction. They are typically electron-deficient, which enhances their reactivity towards the electron-rich diene. Common examples include alkenes and alkynes, often substituted with electron-withdrawing groups to increase their reactivity in the cycloaddition process.
추천 영상:
09:48
General Features
관련 실천
교과서 질문

We predicted that the products would have a 1,2- or 1,4-relationship of the proper substituents. Draw the charge-separated resonance forms of the reactants to support these predictions.

(a) (b)

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교과서 질문

What dienes and dienophiles would react to give the following Diels–Alder products?

(d)

(e)

(f)

1015
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교과서 질문

Predict the major product for each proposed Diels–Alder reaction. Include stereochemistry where appropriate.

(a)

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교과서 질문

Predict the products of the following proposed Diels–Alder reactions.

(d)

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교과서 질문

Predict the products of the following proposed Diels–Alder reactions.

(e)

1446
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교과서 질문

Predict the products of the following proposed Diels–Alder reactions.

(f)

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