Organic Chemistry: Aldehyde Synthesis Reactions

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Questions and Answers

What is the chemical equation for the reaction of benzene with carbon monoxide and hydrogen chloride in the presence of anhydrous AlCl3 / CuCl?

C6H6 + CO + HCl -> C6H5CHO + H2O

What is the chemical equation for the reaction of an alkyl or aryl cyanide with tin(II) chloride and hydrochloric acid followed by hydrolysis?

RCN + SnCl2 + HCl -> RCH=NH -> RCHO

What is the chemical equation for the reduction of an acid chloride with diisobutylaluminium hydride (DIBAL-H) followed by hydrolysis?

R-COCl + DIBAL-H -> R-CH=O

State the type of reaction used in the Rosenmund reaction, along with the reagent used.

<p>Catalytic hydrogenation, using Palladium (Pd) on Barium Sulfate (BaSO4) with a poisoned catalyst.</p> Signup and view all the answers

Flashcards

Gattermann-Koch Reaction

Benzene reacts with carbon monoxide (CO) and hydrogen chloride (HCl) in the presence of a catalyst (like AlCl3 or CuCl) to produce benzaldehyde or substituted benzaldehydes.

Stephen Reaction

Acyl or aryl cyanides are reduced to imines, then hydrolyzed to form aldehydes using stannous chloride (SnCl2) and hydrogen chloride (HCl) in ether solution.

Rosenmund Reaction

Acyl chlorides are reduced to aldehydes with hydrogen (H2) in the presence of palladium on barium sulfate (Pd/BaSO4) catalyst in xylene.

Acyl Chloride

A functional group with the general formula R-COCl; a type of organic compound.

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Aldehyde

An organic compound containing a carbonyl group (C=O) bonded to a hydrogen atom and an alkyl or aryl group.

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Benzaldehyde

An aldehyde derived from benzene by replacing a hydrogen atom with a formyl substituent (–CHO).

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Catalyst

A substance that increases the rate of a chemical reaction without being consumed in the process.

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Study Notes

Gattermann-Koch Reaction

Benzene reacts with carbon monoxide and hydrogen chloride in the presence of anhydrous aluminum chloride/copper chloride to form benzaldehyde or substituted benzaldehydes.

Stephen Reaction

Alkyl or aryl cyanides in ethereal solution are reduced with stannous chloride and hydrochloric acid. This forms an intermediate, which is then hydrolyzed with water to produce aldehydes.

Rosenmund Reduction

Acyl chlorides are reduced to aldehydes using hydrogen gas in the presence of palladium on barium sulfate (Pd/BaSO4) catalyst. This reaction is carried out in xylene.
Different acyl chlorides (CH₃COCl, C₆H₅COCl) produce the corresponding aldehydes (CH₃CHO, C₆H₅CHO).