Sign in
12thPass logo
New chatPYQ LibraryDoubtsRank report
Sign in to see Recents

Your guest activity stays on this device

Sign in to save progress →
Sign in

Aldehydes Ketones and Carboxylic Acids question

2005 · Shift 0 · Q28
Guest · filters and generic practice availableBrowsing as a guest · PYQ filters and generic practice are available. Sign in only for personalised features and saved progress.
  1. PYQ Library
  2. /JEE Main
  3. /Chemistry
  4. /Aldehydes Ketones and Carboxylic Acids
  5. /2005 · Shift 0 · Q28

Aldehydes Ketones and Carboxylic Acids question

2005 · Shift 0 · Q28

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
ppp-cresol reacts with chloroform in alkaline medium to give the compound A which adds hydrogen cyanide to form, the compound B.B.B. The latter on acidic hydrolysis gives chiral carboxylic acid. The structure of the carboxylic acid is :
  1. A
    AIEEE 2005 Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 228 English Option 1
  2. B
    AIEEE 2005 Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 228 English Option 2
  3. C
    AIEEE 2005 Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 228 English Option 3
  4. D
    AIEEE 2005 Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 228 English Option 4
View written solutionFree

Correct answer: C

  1. Identify the first reaction: Reimer–Tiemann reaction

ppp-Cresol is 444-methylphenol. When phenols react with chloroform in alkaline medium, they undergo the Reimer–Tiemann reaction, introducing a formyl group (−CHO-CHO−CHO) mainly at the ortho position to −OH-OH−OH.

So, ppp-cresol gives:

A=2-hydroxy-5-methylbenzaldehydeA = 2\text{-hydroxy-}5\text{-methylbenzaldehyde}A=2-hydroxy-5-methylbenzaldehyde

(One ortho position is equivalent to the other due to symmetry in ppp-cresol.)


  1. Addition of HCN to aldehyde

Aldehyde AAA reacts with HCN to form a cyanohydrin:

Ar−CHO→HCNAr−CH(OH)CNAr-CHO \xrightarrow{HCN} Ar-CH(OH)CNAr−CHOHCN​Ar−CH(OH)CN

Thus,

B=2-hydroxy-5-methylphenyl-CH(OH)CNB = 2\text{-hydroxy-}5\text{-methylphenyl-}CH(OH)CNB=2-hydroxy-5-methylphenyl-CH(OH)CN

The carbon bearing OHOHOH and CNCNCN is attached to four different groups:

  • HHH
  • OHOHOH
  • CNCNCN
  • aryl group

So this carbon is stereogenic.


  1. Acidic hydrolysis of cyanohydrin

On acidic hydrolysis, the nitrile group −CN-CN−CN converts into carboxylic acid −COOH-COOH−COOH:

Ar−CH(OH)CN→H+/H2OAr−CH(OH)COOHAr-CH(OH)CN \xrightarrow{H^+/H_2O} Ar-CH(OH)COOHAr−CH(OH)CNH+/H2​O​Ar−CH(OH)COOH

Therefore the final product is:

2-hydroxy-5-methylphenyl-CH(OH)COOH2\text{-hydroxy-}5\text{-methylphenyl-}CH(OH)COOH2-hydroxy-5-methylphenyl-CH(OH)COOH

This is an α\alphaα-hydroxy acid.


  1. Why is it chiral?

The carbon containing OHOHOH is attached to:

  • HHH
  • OHOHOH
  • COOHCOOHCOOH
  • substituted aryl group

All four groups are different, so the acid is chiral.


  1. Required structure

Hence the carboxylic acid must be:

HO–C6H3(CH3)−CH(OH)COOH\boxed{\text{HO–}C_6H_3(CH_3)-CH(OH)COOH}HO–C6​H3​(CH3​)−CH(OH)COOH​

with substituents corresponding to the product from ortho-formylation of ppp-cresol, i.e. 2-hydroxy-5-methylmandelic acid.

So the correct option is C.


  1. Comparison with stored answer

Stored correct answer: C

Derived answer: C

They agree.

PreviousNext

More from Aldehydes Ketones and Carboxylic Acids

  • Among the following acids which has the lowest pKa value?2005 · MCQ
  • On mixing ethyl acetate with aqueous sodium chloride, the composition of the resultant solution is2004 · MCQ
  • Which of the following undergoes reaction with 50% sodium hydroxide solution to give the corresponding alcohol and acid?2004 · MCQ
  • Which one of the following reduced with zinc and hydrochloric acid to give the corresponding hydrocarbon?2004 · MCQ
  • When CH2​ = CH - COOH is reduced with LiAlH4​, the compound obtained will be2003 · MCQ
  • The reaction of chloroform with alcoholic KOH and p-toluidine forms2003 · MCQ
  • Includes diagram2002 · MCQ
  • Picric acid is :2002 · MCQ