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Organic Chemistry 2: Alcohol Synthesis
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Grignard addition to formaldehyde gives a primary alcohol.
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Grignard addition to an aldehyde gives a secondary alcohol.
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Grignard addition to a ketone gives a tertiary alcohol.
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The OR' group leaves and two equivalents of Grignard add.
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Acid chlorides react twice with Grignard reagents.
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Ethylene oxide opening gives a primary alcohol with two added carbons.
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Organolithium reagents behave like strong carbon nucleophiles.
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Organolithium addition to a ketone gives a tertiary alcohol.
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NaBH4 reduces aldehydes to primary alcohols.
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LiAlH4 reduces aldehydes to primary alcohols.
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NaBH4 reduces ketones to secondary alcohols.
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LiAlH4 reduces ketones to secondary alcohols.
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Esters reduce to two alcohol fragments.
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Carboxylic acids reduce to primary alcohols.
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Acid chlorides reduce to primary alcohols with LiAlH4.
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No reaction — NaBH4 is too mild for esters.
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No reaction — NaBH4 is too mild for carboxylic acids.
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Catalytic hydrogenation can reduce aldehydes to primary alcohols.
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Catalytic hydrogenation can reduce ketones to secondary alcohols.
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No reaction — LiAlH4 does not reduce isolated C=C bonds.
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No reaction — NaBH4 does not reduce isolated C=C bonds.
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PCC stops primary alcohol oxidation at the aldehyde.
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Jones reagent oxidizes primary alcohols to carboxylic acids.
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KMnO4 oxidizes primary alcohols to carboxylic acids.
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CrO3 in acid oxidizes primary alcohols to carboxylic acids.
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Secondary alcohols oxidize to ketones.
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Jones reagent oxidizes secondary alcohols to ketones.
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KMnO4 oxidizes secondary alcohols to ketones.
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No reaction — There is no hydrogen on the alcohol-bearing carbon to oxidize.
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No reaction — Tertiary alcohols generally resist oxidation.
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Fischer esterification forms an ester and water.
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Acid chlorides form esters with alcohols.
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Anhydrides react with alcohols to form an ester plus a carboxylic acid.
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Acidic ester hydrolysis gives a carboxylic acid and an alcohol.
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No reaction — The carboxylic acid protonates and destroys the Grignard reagent.
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No reaction — The alcohol protonates and destroys the Grignard reagent.
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No reaction — Water protonates the Grignard reagent.
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No reaction — N-H groups protonate and destroy Grignard reagents.
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No reaction — S-H groups protonate and destroy Grignard reagents.
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No reaction — The acidic terminal alkyne proton is removed by the Grignard reagent.
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Formaldehyde plus Grignard gives a primary alcohol.
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Use an aldehyde plus Grignard, or reduce a ketone if no new C-C bond is needed.
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A ketone plus Grignard gives a tertiary alcohol.
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LiAlH4 reduces esters to two alcohol fragments; NaBH4 is too mild.
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Use PCC to stop primary alcohol oxidation at the aldehyde.
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Jones reagent oxidizes primary alcohols to carboxylic acids.
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KMnO4 oxidizes primary alcohols to carboxylic acids.
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CrO3 in acid oxidizes primary alcohols to carboxylic acids.