Protonation [onium ion formation]

Protonation [onium ion formation] Protonation [onium ion formation] Definition: Addition of a strong acid to an alcohol leads to the formation of its conjugate acid, called onium or (alkyl)oxonium ion. Protonation [onium ion formation] Explained: Alcohols are amphoteric substances which…

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Protection as silyl ethers

Protection as silyl ethers Protection as silyl ethers Definition: Alcohols can be converted into silyl ethers with trimethylsilyl chloride (TMSCl) or similar silly groups such as t-butyldimethylsilyl chloride (TBDMSCl). This is a useful procedure for the protection…

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Partial reduction (Lindlar)

Partial reduction (Lindlar) Partial Reduction (Lindlar) Definition: Hydrogenation of the first π bond using the Lindlar catalyst gives cis alkenes. Partial Reduction (Lindlar) Explained: As we know, using a catalyst…

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Oxidation to ketones [PCC + others]

Oxidation to ketones [PCC + others] Oxidation to ketones [PCC + others] Definition: Treatment of the secondary alcohols with pyridinium chlorochromate (PCC) leads to ketones. Oxidation to ketones [PCC + others] Explained: Because secondary alcohols…

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Oxidation to carboxylic acids [H2CrO4 + others]

Oxidation to carboxylic acids [H2CrO4 + others] Oxidation to carboxylic acids [H2CrO4 + others] Definition: Primary alcohols treated with chromic acid will be converted to carboxylic acid. Oxidation to carboxylic acids [H2CrO4 + others] Explained: Oxidation is a…

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Oxidation to aldehydes [PCC]

Oxidation to aldehydes [PCC] Oxidation to aldehydes [PCC] Definition: Treatment of alcohols with pyridinium chlorochromate (PCC) leads to the formation of the aldehydes. Oxidation to aldehydes [PCC] Explained: When a primary alcohol is treated with chromic acid,…

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Deprotonation [alkoxide formation]

Deprotonation [alkoxide formation] Deprotonation [alkoxide formation] Definition: Treatment with alcohols with bases gives their conjugate bases, called alkoxy ions (alkoxides). Deprotonation [alkoxide formation] Explained: Alcohols are amphoteric substances because they can act both as acids and as bases. Thus, alcohols are acidic…

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Conversion to tosylates/mesylates

Conversion to tosylates/mesylates Conversation to tosylates/mesylates Definition: Treatment of alcohols with p-toluenesulfonyl chloride (TsCl) results in the formation of tosylates, which is an excellent leaving group. Conversation to tosylate/mesylate Explained: As we know, a hydroxyl…

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Conversion to alkyl chlorides [SOCl2]

Conversion to alkyl chlorides [SOCl2] Conversation to alkyl chlorides [SOCl2] Definition: Primary or secondary alcohols can be converted into alkyl chlorides through treatment with SOCl2. Conversation to alkyl chlorides [SOCl2] Explained: Alkyl chlorides can be obtained from…

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Conversion to alkyl bromides [PBr3]

Conversion to alkyl bromides [PBr3] Conversation to alkyl bromides [PBr3] Definition: Treatment of a primary or secondary alcohol with phosphorus tribromides (PBr3) results in alkyl bromides. Conversation to alkyl bromides [PBr3] Explained: Alkyl bromides can be made from alcohols…

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