Step 1: Deduce Compound C.

Chemistry

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Here are the structural formulas for compounds A, B, C, and D based on the provided information:

  • Step 1: Deduce Compound C. Compound C is an alkyne that, upon hydrogenation with a nickel catalyst, yields 2-methylpentane. The structure of 2-methylpentane is CH3_3-CH(CH3_3)-CH2_2-CH2_2-CH3_3. Compound C does not react with sodamide (NaNH2_2) or ammoniacal silver nitrate, indicating it is an internal alkyne (the triple bond is not at the end of the carbon chain). Considering the 2-methylpentane skeleton, the only possible internal alkyne is 4-methylpent-2-yne.

    CH3−C≡C−CH(CH3)−CH3\text{CH}_3-\text{C}\equiv\text{C}-\text{CH}(\text{CH}_3)-\text{CH}_3

    Hydrogenation of 4-methylpent-2-yne gives 2-methylpentane.

  • Step 2: Deduce Compound B. Compound B (C6_6H12_{12}Cl2_2) is treated with alcoholic KOH, followed by NaNH2_2, to form compound C (4-methylpent-2-yne). This is a double dehydrohalogenation reaction. For an alkyne to be formed, B must be a dihaloalkane where the halogens are either on adjacent carbons (vicinal dihalide) or on the same carbon (geminal dihalide) that correspond to the triple bond in C. Since C is CH3_3-C≡C-CH(CH3_3)-CH3_3, the halogens in B must be on the carbons that form the triple bond.

    CH3−CHCl−CHCl−CH(CH3)−CH3\text{CH}_3-\text{CHCl}-\text{CHCl}-\text{CH}(\text{CH}_3)-\text{CH}_3

    This is 2,3-dichloro-4-methylpentane.

  • Step 3: Deduce Compound A. Compound A (C6_6H12_{12}) is treated with chlorine in the presence of carbon tetrachloride (CCl4_4) to give compound B (2,3-dichloro-4-methylpentane). This is an addition reaction of Cl2_2 across a double bond. Therefore, A must be an alkene, and the double bond must be located where the chlorine atoms were added in B.

    CH3−CH=CH−CH(CH3)−CH3\text{CH}_3-\text{CH}=\text{CH}-\text{CH}(\text{CH}_3)-\text{CH}_3

    This is 4-methylpent-2-ene. Its formula is C6_6H12_{12}, which matches the given information.

  • Step 4: Deduce Compounds D and E. Ozonolysis of compound A (4-methylpent-2-ene) gives two aldehydes, D and E. Compound E is identified as acetaldehyde (CH3_3CHO). Ozonolysis cleaves the double bond and forms carbonyl compounds.

    CH3−CH=CH−CH(CH3)−CH3→O3, then H2O/ZnCH3CHO+CHO−CH(CH3)−CH3\text{CH}_3-\text{CH}=\text{CH}-\text{CH}(\text{CH}_3)-\text{CH}_3 \xrightarrow{\text{O}_3, \text{ then H}_2\text{O/Zn}} \text{CH}_3\text{CHO} + \text{CHO}-\text{CH}(\text{CH}_3)-\text{CH}_3

    So, E is acetaldehyde (CH3_3CHO). And D is 2-methylpropanal (CH3_3CH(CH3_3)CHO).

Here are the structural formulas:

Structure of A:

CH3−CH=CH−CH(CH3)−CH3\boxed{\text{CH}_3-\text{CH}=\text{CH}-\text{CH}(\text{CH}_3)-\text{CH}_3}

Structure of B:

CH3−CHCl−CHCl−CH(CH3)−CH3\boxed{\text{CH}_3-\text{CHCl}-\text{CHCl}-\text{CH}(\text{CH}_3)-\text{CH}_3}

Structure of C:

CH3−C≡C−CH(CH3)−CH3\boxed{\text{CH}_3-\text{C}\equiv\text{C}-\text{CH}(\text{CH}_3)-\text{CH}_3}

Structure of D:

CH3−CH(CH3)−CHO\boxed{\text{CH}_3-\text{CH}(\text{CH}_3)-\text{CHO}}
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