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

2016 · Shift 1 · Q18
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 Advanced
  3. /Chemistry
  4. /Aldehydes Ketones and Carboxylic Acids
  5. /2016 · Shift 1 · Q18

Aldehydes Ketones and Carboxylic Acids question

2016 · Shift 1 · Q18

JEE AdvancedChemistryAldehydes Ketones and Carboxylic AcidsMultiple correct+4 / −2
The correct statements about of the following reaction sequence is (are) Cumene (C9HC_9HC9​H{}_{12})))⟶(ii) H3O+(i) O2\mathrel{\mathop{\kern0pt\longrightarrow} \limits_{(ii)\,{H_3}{O^ + }}^{(i)\,{O_2}}}(ii)H3​O+⟶(i)O2​​PPP⟶CHCl3/NaOH\mathrel{\mathop{\kern0pt\longrightarrow} \limits_{}^{CHC{l_3}/NaOH}}⟶CHCl3​/NaOH​Q(major)+R(minor)QQ (major) + R (minor) QQ(major)+R(minor)Q⟶PhCH2BrNaOH\mathrel{\mathop{\kern0pt\longrightarrow} \limits_{PhC{H_2}Br}^{NaOH}}PhCH2​Br⟶NaOH​$ S
  1. A
    R is steam volatile.
  2. B
    Q gives dark violet coloration with 1% aqueous FeCl3FeCl_3FeCl3​ solution.
  3. C
    S gives yellow precipitate with 2, 4-dinitrophenylhydrazine.
  4. D
    S gives dark violet coloration with 1% aqueous FeCl3FeCl_3FeCl3​ solution.
View written solutionFree

Correct answer: B, C

  1. Identify compound PPP from cumene oxidation

Cumene undergoes air oxidation followed by acidic hydrolysis by the cumene process:

Cumene→(ii) H3O+(i) O2Phenol+Acetone\text{Cumene} \xrightarrow[(ii)\ H_3O^+]{(i)\ O_2} \text{Phenol} + \text{Acetone}Cumene(i) O2​(ii) H3​O+​Phenol+Acetone

Since the next step is with CHCl3/NaOHCHCl_3/NaOHCHCl3​/NaOH (Reimer–Tiemann reaction), the reactive component must be phenol.

So,

P=phenolP = \text{phenol}P=phenol


  1. Reaction of phenol with CHCl3/NaOHCHCl_3/NaOHCHCl3​/NaOH

Phenol with CHCl3/NaOHCHCl_3/NaOHCHCl3​/NaOH undergoes Reimer–Tiemann reaction to give mainly o-hydroxybenzaldehyde and a small amount of p-hydroxybenzaldehyde.

Thus,

Q=o-hydroxybenzaldehyde(major)Q = o\text{-hydroxybenzaldehyde} \quad (\text{major})Q=o-hydroxybenzaldehyde(major) R=p-hydroxybenzaldehyde(minor)R = p\text{-hydroxybenzaldehyde} \quad (\text{minor})R=p-hydroxybenzaldehyde(minor)


  1. Formation of SSS from QQQ with PhCH2Br/NaOHPhCH_2Br/NaOHPhCH2​Br/NaOH

QQQ is ooo-hydroxybenzaldehyde. In presence of NaOHNaOHNaOH, the phenolic −OH-OH−OH forms phenoxide and reacts with benzyl bromide via Williamson ether synthesis:

o-HO-C6H4−CHO→PhCH2BrNaOHo-PhCH2O−C6H4−CHOo\text{-HO-C}_6H_4-CHO \xrightarrow[PhCH_2Br]{NaOH} o\text{-}PhCH_2O-C_6H_4-CHOo-HO-C6​H4​−CHONaOHPhCH2​Br​o-PhCH2​O−C6​H4​−CHO

So SSS is o-benzyloxybenzaldehyde.


  1. Check each option

Option A: RRR is steam volatile.

RRR is ppp-hydroxybenzaldehyde. Steam volatility is shown prominently by o-hydroxybenzaldehyde due to intramolecular H-bonding and lower association. The para isomer forms intermolecular H-bonding and is not steam volatile.

So, A is false.


Option B: QQQ gives dark violet coloration with 1% aqueous FeCl3FeCl_3FeCl3​ solution.

QQQ is ooo-hydroxybenzaldehyde, which still contains a phenolic −OH-OH−OH group. Phenols give colored complexes with neutral FeCl3FeCl_3FeCl3​.

Hence, B is true.


Option C: SSS gives yellow precipitate with 2,4-dinitrophenylhydrazine.

SSS is ooo-benzyloxybenzaldehyde. It contains an aldehyde group.

Aldehydes and ketones give yellow/orange precipitate with 2,4-DNP reagent.

Hence, C is true.


Option D: SSS gives dark violet coloration with 1% aqueous FeCl3FeCl_3FeCl3​ solution.

In SSS, the phenolic −OH-OH−OH has been converted into a benzyl ether (−OCH2Ph-OCH_2Ph−OCH2​Ph). Therefore, there is no free phenolic group left.

So it will not give the FeCl3FeCl_3FeCl3​ coloration test.

Hence, D is false.


  1. Final answer

Correct statements are:

B, C\boxed{B,\ C}B, C​


  1. Comparison with stored correct answer

Stored correct answer: B,CB, CB,C

My derived answer matches it exactly.

PreviousNext

More from Aldehydes Ketones and Carboxylic Acids

  • Positive Tollen’s test is observed for2016 · Multiple correct
  • The major product of the following reaction sequence is: Includes diagram2016 · MCQ
  • Reagent(s) which can be used to bring about the following transformation is(are) Includes diagram2016 · Multiple correct
  • The correct order of acidity for the following compounds is Includes diagram2016 · MCQ
  • The major product of the following reaction is Includes diagram2015 · Multiple correct
  • In the following reactions Compound X is Includes diagram2015 · Multiple correct
  • In the following reactions The major compound Y is Includes diagram2015 · Multiple correct
  • Among the following the number of reactions that produces benzaldehyde is ​. Includes diagram2015 · Numerical