MCQMediumJEE 2026Isomerism (Structural, Stereoisomerism)

JEE Chemistry 2026 Question with Solution

Given below are four compounds :

(a) n-propyl chloride

(b) iso-propyl chloride

(c) sec-butyl chloride

(d) neo-pentyl chloride

Percentage of carbon in the one which exhibits optical isomerism is :

  • A

    5656

  • B

    4040

  • C

    4646

  • D

    5252

Answer

Correct answer:D

Step-by-step solution

Standard Method

Given: Four compounds are listed: n-propyl chloride, iso-propyl chloride, sec-butyl chloride, and neo-pentyl chloride.

Find: The percentage of carbon in the compound that exhibits optical isomerism.

A compound shows optical isomerism when it contains a chiral carbon bonded to four different groups.

From the given compounds:

  • n-propyl chloride: CH3CH2CH2ClCH_3CH_2CH_2Cl has no chiral carbon.
  • iso-propyl chloride: (CH3)2CHCl(CH_3)_2CHCl has no chiral carbon.
  • sec-butyl chloride: CH3CH(Cl)CH2CH3CH_3CH(Cl)CH_2CH_3 has a carbon attached to HH, ClCl, CH3CH_3, and C2H5C_2H_5, so it is chiral.
  • neo-pentyl chloride: (CH3)3CCH2Cl(CH_3)_3CCH_2Cl has no chiral carbon.

Therefore, the required compound is sec-butyl chloride with molecular formula C4H9ClC_4H_9Cl.

Now calculate the mass percentage of carbon:

%C=Mass of Carbon atomsMolar mass of the compound×100\%C = \frac{\text{Mass of Carbon atoms}}{\text{Molar mass of the compound}} \times 100

Mass of carbon:

4×12=484 \times 12 = 48

Molar mass of C4H9ClC_4H_9Cl:

48+9+35.5=92.548 + 9 + 35.5 = 92.5

So,

%C=4892.5×10051.89%\%C = \frac{48}{92.5} \times 100 \approx 51.89\%

Rounding to the nearest integer:

52%52\%

Therefore, the correct option is D.

Identify the chiral compound first

Given: The four compounds are compared for optical isomerism.

Find: Which one is optically active and then its carbon percentage.

The key idea is that optical isomerism requires a carbon attached to four different substituents.

In sec-butyl chloride, the relevant carbon is bonded to:

  • HH
  • ClCl
  • CH3CH_3
  • CH2CH3CH_2CH_3

Since all four groups are different, this carbon is chiral. The other listed chlorides do not contain such a carbon.

Hence the compound is sec-butyl chloride, C4H9ClC_4H_9Cl.

Now compute carbon percentage using atomic masses C=12C = 12, H=1H = 1, and Cl=35.5Cl = 35.5:

Mass of carbon=4×12=48\text{Mass of carbon} = 4 \times 12 = 48 Total molar mass=(4×12)+(9×1)+35.5=92.5\text{Total molar mass} = (4 \times 12) + (9 \times 1) + 35.5 = 92.5 %C=4892.5×10051.89\%C = \frac{48}{92.5} \times 100 \approx 51.89

Thus the percentage of carbon is approximately 5252, so the correct option is D.

Common mistakes

  • Mistake: Assuming every secondary alkyl chloride shows optical isomerism. Why it is wrong: a chiral center requires four different groups on the carbon. What to do instead: check all four substituents explicitly before declaring the molecule optically active.

  • Mistake: Marking iso-propyl chloride as chiral. Why it is wrong: the central carbon is attached to two identical CH3CH_3 groups, so it is not a stereogenic center. What to do instead: look for repeated groups around the candidate carbon.

  • Mistake: Using the wrong molecular formula for sec-butyl chloride. Why it is wrong: an incorrect formula gives the wrong molar mass and wrong carbon percentage. What to do instead: write the structure carefully and count atoms to get C4H9ClC_4H_9Cl.

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