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Complete the missing links CH(3)CHBrCH...

Complete the missing links
`CH_(3)CHBrCH_(3) overset("alc. KOH")rarr Xoverset("HBr, Peroxide")rarr Y overset(CH_(3)ONa)rarr Z`

A

`{:("X","Y","Z"),(CH_(3)CH=CH_(2),CH_(3)CH(Br)CH_(2)Br,CH_(3)CH(OH)CH_(3)):}`

B

`{:("X","Y","Z"),(CH_(3)CH=CH_(2),CH_(3)CH_(2)CH_(2)Br,CH_(3)CH_(2)OCH_(2)CH_(3)):}`

C

`{:("X","Y","Z"),(CH_(3)CH=CH_(2),CH_(3)CH(Br)CH_(3),CH_(3)CH_(2)OCH_(2)CH_(3)):}`

D

`{:("X","Y","Z"),(CH_(3)CH=CH_(2),CH_(3)CH_(2)CH_(2)Br,CH_(3)CH_(2)CH_(2)OCH_(3)):}`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem, we need to identify the compounds X, Y, and Z in the given reaction sequence. Let's break down the steps: ### Step 1: Identify Compound X We start with the compound \( CH_3CHBrCH_3 \) and treat it with alcoholic KOH. - **Reaction Type**: Alcoholic KOH is a strong base and promotes elimination reactions (dehydrohalogenation). - **Elimination**: The elimination of HBr occurs, where the Br leaves and a hydrogen atom from the adjacent carbon is also removed. The structure of the starting compound can be represented as: ``` CH3 | CHBr | CH3 ``` After elimination, we will form a double bond between the first and second carbon atoms: ``` CH3 | CH=CH2 ``` Thus, compound X is: \[ X = CH_3CH=CH_2 \] ### Step 2: Identify Compound Y Next, we treat compound X with HBr in the presence of peroxide. - **Reaction Type**: The presence of peroxide leads to the anti-Markovnikov addition of HBr. - **Mechanism**: The bromine atom will add to the less substituted carbon atom (the one with more hydrogen atoms), while the hydrogen will add to the more substituted carbon. Starting with: ``` CH3 | CH=CH2 ``` The addition of HBr will yield: ``` CH3 | CH2Br ``` Thus, compound Y is: \[ Y = CH_3CH_2CH_2Br \] ### Step 3: Identify Compound Z Finally, we treat compound Y with \( CH_3ONa \) (sodium methoxide). - **Reaction Type**: This reaction is a Williamson ether synthesis. - **Mechanism**: The bromine atom is a good leaving group and will leave, allowing the methoxide ion (\( CH_3O^- \)) to attack the carbon atom where the bromine was attached. Starting with: ``` CH3 | CH2Br ``` After the reaction, we get: ``` CH3 | CH2OCH3 ``` Thus, compound Z is: \[ Z = CH_3CH_2CH_2OCH_3 \] ### Summary of Compounds - **X**: \( CH_3CH=CH_2 \) - **Y**: \( CH_3CH_2CH_2Br \) - **Z**: \( CH_3CH_2CH_2OCH_3 \)
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