Grignard addition co reactant

Overview

Methanal plus a Grignard reagent gives a primary alcohol after acidic work-up.

Transformation

Methanal → Primary alcohols

Equation

HCHO + R-MgX -> R-CH2OMgX; then H3O+ -> R-CH2OH

Reagents

Grignard reagent, then dilute acid

Environment

dry ether, then acidic work-up

Reaction class

nucleophilic addition

Mechanism

Grignard carbonyl addition

Evidence level

textbook core

Scope and limitations

Scope

Methanal is the carbonyl co-reactant that gives primary alcohols after Grignard addition and acidic work-up.

Limitations

This record represents the methanal co-reactant branch of Grignard addition; it should share the Grignard-to-primary-alcohol mechanism family rather than becoming a separate unsupported drawing.

Related reactions

• Controlled oxidation: Primary alcohols → Aldehydes

  Controlled oxidation of a primary alcohol gives an aldehyde.

• Complete oxidation: Primary alcohols → Carboxylic acids

  Full oxidation of a primary alcohol gives a carboxylic acid.

• Reduction: Aldehydes → Primary alcohols

  Reduction of an aldehyde gives a primary alcohol.

• Reduction: Carboxylic acids → Primary alcohols

  Reduction of a carboxylic acid gives a primary alcohol.

• Carbonyl addition: Grignard reagents → Primary alcohols

  Grignard addition to methanal gives primary alcohols after work-up.

• Catalytic oxidation: Methanol → Methanal

  Removing hydrogen from methanol creates a carbonyl while retaining its single carbon. Oxygen accepts the removed hydrogen as water in this overall catalytic-oxidation equation.

• Carbonyl reduction: Methanal → Methanol

  Hydride addition forms a new C-H bond and converts the C=O pi bond into an alkoxide. Protonation then gives methanol without introducing another carbon.

• Aldehyde oxidation: Methanal → Methanoic acid

  Oxidation changes the aldehyde hydrogen into acid functionality through the hydrated carbonyl. The carbon count stays at one, but further oxidation remains possible.

References

1. Organic Chemistry: Nucleophilic Addition of Hydride and Grignard ReagentsJohn McMurry · OpenStax Organic Chemistry · 2023

   Supports Grignard carbon nucleophiles adding to aldehydes and ketones to give alkoxide intermediates, followed by protonation during acidic work-up.