JEE Main · 2024 · Shift-IhardHALO-054

In the following sequence of reaction, the major products B and C respectively are:

Haloalkanes & Haloarenes · Class 12 · JEE Main Previous Year Question

Question

In the following sequence of reaction, the major products B and C respectively are: image

Options
  1. a

    Option A

  2. b

    Option B

  3. c

    Option C

  4. d

    Option D

Correct Answera

Option A

Detailed Solution

Step 1: Reaction with Na/Et₂O (Wurtz coupling)

Cyclobutyl bromide + Na → Wurtz reaction → coupled product

\ce2C4H7Br+2Na>[Et2O]C4H7C4H7+2NaBr\ce{2 C4H7Br + 2 Na ->[Et2O] C4H7-C4H7 + 2 NaBr}

Product A = Bicyclobutane (two cyclobutane rings joined)

Step 2: Grignard formation and deuterolysis

Product A + Mg in ether → Grignard reagent

Then reaction with \ceD2O\ce{D2O} (deuterium oxide):

\ceRMgR+D2O>RD+RD+Mg(OD)2\ce{R-Mg-R + D2O -> R-D + R-D + Mg(OD)2}

This replaces the C-Mg bonds with C-D bonds.

Product B = Deuterated cyclobutane (\ceC4H7D\ce{C4H7D})

Structure: Cyclobutane with D replacing H at the position where Br was originally.

Step 3: Reaction with CoF₂ (Swarts reaction)

Cyclobutyl bromide + \ceCoF2\ce{CoF2}halogen exchange → fluoride

\ceC4H7Br+CoF2>C4H7F+CoBr2\ce{C4H7Br + CoF2 -> C4H7F + CoBr2}

Product C = Cyclobutyl fluoride

Structure: Cyclobutane with F at the position where Br was.

Answer: (a)

Key Reactions:

  1. Wurtz coupling: \ce2RX+2Na>RR+2NaX\ce{2 R-X + 2 Na -> R-R + 2 NaX}
  2. Grignard + D₂O: \ceRMgX+D2O>RD\ce{R-MgX + D2O -> R-D} (deuteration)
  3. Swarts reaction: \ceRX+MF>RF\ce{R-X + MF -> R-F} (halogen exchange to fluoride)

Note: Deuterium (D or ²H) is used as a tracer isotope of hydrogen.

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In the following sequence of reaction, the major products B and C respectively are: (JEE Main 2024) | Canvas Classes