Chemistry · Aldehydes and Ketones

JEE Main 2024 — 1 February, Shift 1 — Question 73

Match List - I with List -II

List - I (Reactions)List - II (Reagents)
(A)CH3(CH2)3−C−OC2H5→CH2(CH2)3CHO                                        ∥∥                                        O\begin{aligned}& C{{H}_{3}}{{(C{{H}_{2}})}_{3}}-C-O{{C}_{2}}{{H}_{5}}\to C{{H}_{2}}{{(C{{H}_{2}})}_{3}}CHO\\&\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\|\| \\ & \,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,O \\ \end{aligned}(I)CH3MgBr,H2O\text{C}{{\text{H}}_{3}}\text{MgBr},{{\text{H}}_{2}}\text{O}
(B)C6H5COC6H5→C6H5CH2C6H5{{\text{C}}_{6}}{{\text{H}}_{5}}\text{CO}{{\text{C}}_{6}}{{\text{H}}_{5}}\to {{\text{C}}_{6}}{{\text{H}}_{5}}\text{C}{{\text{H}}_{2}}{{\text{C}}_{6}}{{\text{H}}_{5}}(II)Zn(Hg)\text{Zn}\left( \text{Hg} \right) and conc. HCl
(C)C6H5CHO→C6H5CH(OH)CH3{{\text{C}}_{6}}{{\text{H}}_{5}}\text{CHO}\to {{\text{C}}_{6}}{{\text{H}}_{5}}\text{CH}\left( \text{OH} \right)\text{C}{{\text{H}}_{3}}(III)NaBH4,H+\text{NaB}{{\text{H}}_{4}},{{\text{H}}^{+}}
(D)CH2C0CH2COOC2H5→CH2C(OH)CH2COOC2H5                                                                                       ∥                                                                                      H\begin{aligned}& C{{H}_{2}}C0C{{H}_{2}}COO{{C}_{2}}{{H}_{5}}\to C{{H}_{2}}C(OH)C{{H}_{2}}COO{{C}_{2}}{{H}_{5}} \\ & \,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\| \\ & \,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,H \\ \end{aligned}(IV)DIBAL-H, H2O{{\text{H}}_{2}}\text{O}

Choose the correct answer from options given below:

  1. Option A:

    A-(III), (B)-(IV), (C)-(I), (D)-(II)

  2. Option B:

    A-(IV), (B)-(II), (C)-(I), (D)-(III)

    Correct
  3. Option C:

    A-(IV), (B)-(II), (C)-(III), (D)-(I)

  4. Option D:

    A-(III), (B)-(IV), (C)-(II), (D)-(I)

Answer: B

Step-by-step solution

CH3(CH2)5COOC2H5→ DIBAL-H, H2OCH3(CH2)5CHO\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{5} \mathrm{COOC}_{2} \mathrm{H}_{5} \xrightarrow{\text { DIBAL-H, } \mathrm{H}_{2} \mathrm{O}} \mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{5} \mathrm{CHO}

C6H5COC6H5→Zn(Hg)& conc. HClC6H5CH2C6H5\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COC}_{6} \mathrm{H}_{5} \xrightarrow{\mathrm{Zn}(\mathrm{Hg}) \& \text { conc. } \mathrm{HCl}} \mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{C}_{6} \mathrm{H}_{5}

C6H5CHO→H2OCH3MgBrC6H5CH(OH)CH3\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CHO} \xrightarrow[\mathrm{H}_{2} \mathrm{O}]{\mathrm{CH}_{3} \mathrm{MgBr}} \mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}(\mathrm{OH}) \mathrm{CH}_{3}

CH3COCH2COOC2H5→NaBH4,H+CH3CH(OH)CH2COOC2H5\mathrm{CH}_{3} \mathrm{COCH}_{2} \mathrm{COOC}_{2} \mathrm{H}_{5} \xrightarrow{\mathrm{NaBH}_{4}, \mathrm{H}^{+}} \mathrm{CH}_{3} \mathrm{CH}(\mathrm{OH}) \mathrm{CH}_{2} \mathrm{COOC}_{2} \mathrm{H}_{5}

Answer key and solution verified before publishing.

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Exam
JEE Main 2024
Subject
Chemistry
Chapter
Aldehydes and Ketones
Topic
Introduction and Preparation of Aldehydes and Ketones