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Number of Dichloro Compounds from Photochemical Monochlorination of n Butane

n-Butane on monochlorination under photochemical condition gives an optically active compound "P". "P" on further chlorination gives dichloro compounds.

The number of dichloro compounds obtained (ignore stereoisomers) is :

Options

A

3

B

4

Correct
C

5

D

6

Step-by-Step Solution

To determine the number of dichloro compounds obtained, we analyze the reaction step-by-step:

Step 1: Identification of Compound "P"

Monochlorination of nn-butane (CH3CH2CH2CH3\text{CH}_3-\text{CH}_2-\text{CH}_2-\text{CH}_3) gives two structural isomers:

  1. 1-chlorobutane (CH3CH2CH2CH2Cl\text{CH}_3-\text{CH}_2-\text{CH}_2-\text{CH}_2\text{Cl}): It does not possess any chiral center, making it optically inactive.
  2. 2-chlorobutane (CH3CH2CH(Cl)CH3\text{CH}_3-\text{CH}_2-\overset{*}{\text{C}}\text{H(Cl)}-\text{CH}_3): The second carbon (C2\text{C}_2) is attached to four different groups (H-\text{H}, Cl-\text{Cl}, CH3-\text{CH}_3, and CH2CH3-\text{CH}_2\text{CH}_3), making it a chiral center and thus optically active.

Since compound "P" is optically active, P must be 2-chlorobutane.


Step 2: Further Chlorination of Compound "P"

The structure of 2-chlorobutane is: C4H3C3H2C2H(Cl)C1H3\overset{4}{\text{C}}\text{H}_3-\overset{3}{\text{C}}\text{H}_2-\overset{2}{\text{C}}\text{H(Cl)}-\overset{1}{\text{C}}\text{H}_3

Replacing a hydrogen atom with a chlorine atom at each distinct carbon position gives the following dichloro compounds:

  1. Substitution at C1\text{C}_1: CH3CH2CH(Cl)CH2Cl    1,2-dichlorobutane\text{CH}_3-\text{CH}_2-\text{CH(Cl)}-\text{CH}_2\text{Cl} \quad \implies \text{1,2-dichlorobutane}

  2. Substitution at C2\text{C}_2: CH3CH2C(Cl)2CH3    2,2-dichlorobutane\text{CH}_3-\text{CH}_2-\text{C(Cl)}_2-\text{CH}_3 \quad \implies \text{2,2-dichlorobutane}

  3. Substitution at C3\text{C}_3: CH3CH(Cl)CH(Cl)CH3    2,3-dichlorobutane\text{CH}_3-\text{CH(Cl)}-\text{CH(Cl)}-\text{CH}_3 \quad \implies \text{2,3-dichlorobutane}

  4. Substitution at C4\text{C}_4: ClCH2CH2CH(Cl)CH3    1,3-dichlorobutane\text{ClCH}_2-\text{CH}_2-\text{CH(Cl)}-\text{CH}_3 \quad \implies \text{1,3-dichlorobutane}


Step 3: Total Count

Ignoring stereoisomers, the unique structural isomers formed are:

  1. 1,21,2-dichlorobutane
  2. 2,22,2-dichlorobutane
  3. 2,32,3-dichlorobutane
  4. 1,31,3-dichlorobutane

Thus, the total number of dichloro compounds obtained is 4.

Correct Option: B

Number of Dichloro Compounds from Photochemical Monochlorination of n Butane | Chemistry PYQ Solution - JEE Challenger