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Which of the following dienes is chiral?...

Which of the following dienes is chiral?

A

`CH_(3)-CH=C=CH_(2)`

B

`CH_(3)-CH=CH-CH=CH_(2)`

C

`CH_(3)-CH=C=CH-CH_(3)`

D

`CH_(2)=CH-CH_(2)-CH=CH_(2)`

Text Solution

AI Generated Solution

The correct Answer is:
To determine which of the given dienes is chiral, we need to analyze each compound for the presence of a plane of symmetry. A compound is chiral if it does not have a plane of symmetry. Let's go through the options step by step. ### Step 1: Analyze Compound A - **Compound A**: CH3CH=CH=CH2 - This compound is an allene. In an allene, the central carbon atoms are sp-hybridized and the molecule can be represented as: ``` CH3 - C=C=C - H ``` - The two terminal groups (hydrogens) on one end are identical. - **Conclusion**: There is a plane of symmetry in this compound. Therefore, it is **not chiral**. ### Step 2: Analyze Compound B - **Compound B**: CH3CH=CH-CH=CH2 - This compound is a conjugated diene. The structure can be visualized as: ``` CH3 - CH = CH - CH = CH2 ``` - The presence of the CH3 group in the plane means that there is a plane of symmetry that bisects the molecule. - **Conclusion**: This compound has a plane of symmetry and is **not chiral**. ### Step 3: Analyze Compound C - **Compound C**: CH3CH=C=CHCH3 - This compound can also be viewed as an allene with different groups at the terminal carbon atoms: ``` CH3 - C = C - CH3 ``` - Here, both terminal carbons have different groups (CH3 and H). - **Conclusion**: There is no plane of symmetry in this compound, making it **chiral**. ### Step 4: Analyze Compound D - **Compound D**: CH2=CH-CH2-CH=CH2 - The structure can be represented as: ``` CH2 = CH - CH2 - CH = CH2 ``` - This compound has a central carbon with two identical groups (hydrogens). - **Conclusion**: There is a plane of symmetry in this compound, so it is **not chiral**. ### Final Answer The only chiral compound among the given options is **Compound C**.

To determine which of the given dienes is chiral, we need to analyze each compound for the presence of a plane of symmetry. A compound is chiral if it does not have a plane of symmetry. Let's go through the options step by step. ### Step 1: Analyze Compound A - **Compound A**: CH3CH=CH=CH2 - This compound is an allene. In an allene, the central carbon atoms are sp-hybridized and the molecule can be represented as: ``` CH3 - C=C=C - H ``` ...
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