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Basics of Organic Chemistry question

2014 · Shift 1 · Q13
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Basics of Organic Chemistry question

2014 · Shift 1 · Q13

JEE AdvancedChemistryBasics of Organic ChemistryMultiple correct+3 / −1
The correct combination of names for isomeric alcohols with molecular formula C4HC_4HC4​H{}_{10}$O is/are
  1. A
    tert-butanol and 2-methylpropan-2-ol
  2. B
    tert-butanol and 1, 1-dimethylethan-1-ol
  3. C
    n-butanol and butan-1-ol
  4. D
    iso-butyl alcohol and 2-methylpropan-1-ol
View written solutionFree

Correct answer: A, C, D

  1. List the alcohol isomers of C4H10OC_4H_{10}OC4​H10​O

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

  • butan-1-ol
  • butan-2-ol
  • 2-methylpropan-1-ol
  • 2-methylpropan-2-ol

The question asks for correct combinations of names for isomeric alcohols, i.e. two names referring to the same valid alcohol.


  1. Check each option

Option A: tert-butanol and 2-methylpropan-2-ol

  • tert-butanol is the common name of (CH3)3COH(CH_3)_3COH(CH3​)3​COH
  • Its IUPAC name is 2-methylpropan-2-ol.

So, A is correct.


Option B: tert-butanol and 1,1-dimethylethan-1-ol

  • tert-butanol is indeed 222-methylpropan-222-ol.
  • The name 1,1-dimethylethan-1-ol is not the correct IUPAC name.

Why?

Structure implied by this name would be equivalent to: CH3−C(OH)(CH3)2CH_3-C(OH)(CH_3)_2CH3​−C(OH)(CH3​)2​ which simplifies to tert-butanol, but according to IUPAC rules we must choose the longest chain containing the −OH-OH−OH group. That gives propan-2-ol as parent chain with a methyl substituent at carbon 222: 2-methylpropan-2-ol2\text{-methylpropan-}2\text{-ol}2-methylpropan-2-ol

Hence the given name is not acceptable here.

So, B is incorrect.


Option C: n-butanol and butan-1-ol

  • n-butanol is the common name for the straight-chain primary butyl alcohol: CH3CH2CH2CH2OHCH_3CH_2CH_2CH_2OHCH3​CH2​CH2​CH2​OH
  • Its IUPAC name is butan-1-ol.

So, C is correct.


Option D: iso-butyl alcohol and 2-methylpropan-1-ol

  • iso-butyl alcohol has structure (CH3)2CHCH2OH(CH_3)_2CHCH_2OH(CH3​)2​CHCH2​OH
  • Its IUPAC name is 2-methylpropan-1-ol.

So, D is correct.


  1. Final selection

The correct options are: A, C, D\boxed{A,\ C,\ D}A, C, D​


  1. Comparison with stored correct answer

Stored correct answer: A, C, D

My derived answer: A, C, D

They match.

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