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Question: Draw the major product for the following reaction, showing the stereochemistry by using wedge bonds. The product will be racemic, but show only one enantiomer. (Remember that a hydrogen atom on a chirality center must be shown explicitly and with a wedge/hash bond.)– Free Chegg Question Answer

Draw the major product for the following reaction, showing the stereochemistry by using wedge bonds. The product will be racemic, but show only one enantiomer. (Remember that a hydrogen atom on a chirality center must be shown explicitly and with a wedge/hash bond.)

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Answer:

Answer



General guidance

Concepts and reason

The concept used to solve this problem is addition to the double bond. The alkene is reacted with a halogen and ethanol molecule to form a halohydrin. Fundamentals

Addition of an electrophile, that is, chlorine to the double bond forms a bridged chloronium ion followed by the nucleophilic attack by the ethanol molecule from the back side, that is, anti-addition takes place. Show more First Step | All Steps | Answer Only

Step-by-step

Step 1 of 2

The reaction is as follows:

11lllllll
dat
....1111H

Explanation | Hint for next step

Treatment of (Z)-but-2-en-2-ylcyclohexane with the chlorine molecule gives chloronium ion as an intermediate. Here, Cl-Cl bond cleaves heterolytically and forms chloride ion. This step is the rate-determining.

Open the ring by the nucleophilic attack of ethanol from back side.

Step 2 of 2

The formation of products is as follows:

CH3CH OH

Here, racemic mixture will be formed but only product (one enantiomer) is shown.

The major product is,

O111111

Explanation

The ethanol molecule opens the chloronium ion intermediate at more substituted carbon from back side to form halohydrin. So, the stereochemistry at that carbon is inverted as shown below:

Answer

The major product is,

O111111

Answer only

The major product is,

O111111

11lllllll dat ….1111H CH3CH OH RE CH3CH OH O111111 O111111

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