organic chemistry

Question

organic chemistry

Manu · Accepted Answer

Step 1:

Retrosynthesis

To synthesize vinylbenzene from aniline, the adopted disjuncture are considered:

Diazonium salt shaping: the -NH₂ mathematical group of aniline oil can be win over to a diazonium group ( -N₂⁺ ) by diazotization.
Diminution to benzene: the diazonium group can be replaced with H to reclaim benzine.
Vinylation: a vinyl radical radical ( -CH= CH₂ ) can be lent to benzene via a palladium - catalyse heck reaction with vinyl radical halide ( e.g., vinyl radical bromide ).

Explanation:

Disclose the target molecule into two step : replace the aminic group ( -NH₂ ) with hydrogen via diazotization and reduction, follow by add together a vinyl radical grouping ( -CH= CH₂ ) through a heck pair reaction.

Step 2:

Forward Synthesis

Starting Material: Begin with aniline (C₆H₅NH₂).
Step 2.1: Diazotization
- The diazonium salt (C₆H₅N₂⁺Cl⁻) is created when aniline and sodium nitrite (NaNO₂) react in hydrochloric acid (HCl) between 0 and 5°C.
- Reaction:
  $ext{C₆H₅NH₂} + NaNO₂ + HCl ightarrow ext{C₆H₅N₂⁺Cl⁻} + H₂O$
Step 2.2: Reduction to Benzene
- Benzene (C₆H₆) is produced by reducing the diazonium salt with hypophosphorous acid (H₃PO₂) to substitute hydrogen for the -N₂⁺ group..
- Reaction:
  $ext{C₆H₅N₂⁺Cl⁻} + H₃PO₂ ightarrow ext{C₆H₆} + N₂ + HCl$
Step 2.3: Vinylation (Heck Reaction)
- React with benzeneIn the presence of a palladium catalyst and a base, react benzene with a vinyl halide (such as vinyl bromide, CH₂=CHBr) to introduce the vinyl group (-CH=CH₂) and create styrene (C₆H₅CH=CH₂).
- Reaction:
  $ext{C₆H₆} + CH₂=CHBr \xrightarrow{ ext{Pd catalyst, base}} ext{C₆H₅CH=CH₂}$

Explanation:

Utilizing diazotization and reduction, convert the aniline derivative to benzene. Attach the vinyl group and create vinylbenzene by performing a heck pair off reaction with vinyl group bromide.

Final Answer:

Chemistry

Chemistry