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Alcohols Phenols and Ethers question

2022 · 29 Jun · Shift 2 · Q21
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Alcohols Phenols and Ethers question

2022 · 29 Jun · Shift 2 · Q21

JEE MainChemistryAlcohols Phenols and EthersNumerical+4 / −1
The number of chiral alcohol(s) with molecular formula C4H10OC_4H_{10}OC4​H10​O is ‾\underline{\hspace{2cm}}​.
Numerical answer
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Correct answer: 1

  1. We need to count chiral alcohols having molecular formula C4H10OC_4H_{10}OC4​H10​O.

  2. First, list all alcohol isomers of C4H10OC_4H_{10}OC4​H10​O (exclude ethers, since the question asks only alcohols).

For C4H10OC_4H_{10}OC4​H10​O, the alcohol isomers are:

  • Butan-1-ol: CH3CH2CH2CH2OHCH_3CH_2CH_2CH_2OHCH3​CH2​CH2​CH2​OH
  • Butan-2-ol: CH3CH(OH)CH2CH3CH_3CH(OH)CH_2CH_3CH3​CH(OH)CH2​CH3​
  • 2-Methylpropan-1-ol: (CH3)2CHCH2OH(CH_3)_2CHCH_2OH(CH3​)2​CHCH2​OH
  • 2-Methylpropan-2-ol: (CH3)3COH(CH_3)_3COH(CH3​)3​COH
  1. Now check chirality of each alcohol.

(i) Butan-1-ol

Structure: CH3CH2CH2CH2OHCH_3CH_2CH_2CH_2OHCH3​CH2​CH2​CH2​OH

No carbon has four different substituents. So, it is achiral.

(ii) Butan-2-ol

Structure: CH3CH(OH)CH2CH3CH_3CH(OH)CH_2CH_3CH3​CH(OH)CH2​CH3​

The second carbon is attached to:

  • OHOHOH
  • HHH
  • CH3CH_3CH3​
  • CH2CH3CH_2CH_3CH2​CH3​

These are four different groups, so this carbon is a chiral center. Hence, butan-2-ol is chiral.

(iii) 2-Methylpropan-1-ol

Structure: (CH3)2CHCH2OH(CH_3)_2CHCH_2OH(CH3​)2​CHCH2​OH

The central carbon is attached to:

  • CH3CH_3CH3​
  • CH3CH_3CH3​
  • CH2OHCH_2OHCH2​OH
  • HHH

Since two groups are identical (CH3CH_3CH3​ and CH3CH_3CH3​), it is not chiral.

(iv) 2-Methylpropan-2-ol

Structure: (CH3)3COH(CH_3)_3COH(CH3​)3​COH

The central carbon is attached to three identical CH3CH_3CH3​ groups, so it is achiral.

  1. Therefore, only one alcohol structure is chiral:
  • Butan-2-ol
  1. Note: Butan-2-ol exists as two enantiomers (R)(R)(R) and (S)(S)(S), but the question asks for the number of chiral alcohol(s), i.e. the number of chiral compounds/structures, not stereoisomers counted separately unless explicitly stated.

So the required number is: 111

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