ochem functional groups & reagents

CH₃-C(=O)-OCH₃: What functional group?

Ester. Look for C=O attached to O-C.

CH₃-C(=O)-CH₃: What functional group?

Ketone. C=O attached to two carbons.

CH₃-CHO: What functional group?

Aldehyde. C=O attached to H.

CH₃-COOH: What functional group?

Carboxylic acid. C=O attached to OH.

CH₃-CONH₂: What functional group?

Amide. C=O attached to nitrogen.

CH₃-C≡N: What functional group?

Nitrile. Carbon triple-bonded to nitrogen.

CH₃-COCl: What functional group?

Acid chloride. C=O attached to Cl.

CH₃-COSCH₃: What functional group?

Thioester. C=O attached to S-CH₃.

CH₃-CH₂-NH₂: What functional group?

Primary amine. NH₂ attached to carbon, not C=O.

CH₃-CH₂OH: Primary or secondary alcohol?

Primary. The OH-bearing carbon has one carbon neighbor.

CH₃-CH(OH)-CH₃: What type of alcohol?

Secondary. The OH-bearing carbon has two carbon neighbors.

(CH₃)₃C-OH: What type of alcohol?

Tertiary. The OH-bearing carbon has three carbon neighbors.

CH₃CH₂OH + PBr₃ → ?

CH₃CH₂Br. OH is replaced by Br.

CH₃CH₂Br + NaCN, DMSO → ?

CH₃CH₂CN. Br is replaced by CN.

CH₃CH₂CN + H₃O⁺, heat → ?

CH₃CH₂COOH. Nitrile hydrolysis gives carboxylic acid.

CH₃CH₂CN + LiAlH₄; H₃O⁺ → ?

CH₃CH₂CH₂NH₂. Nitrile becomes primary amine.

CH₃CN + CH₃MgBr; H₃O⁺ → ?

CH₃COCH₃. Nitrile plus Grignard gives ketone.

CH₃COOH + LiAlH₄; H₃O⁺ → ?

CH₃CH₂OH. Carboxylic acid becomes primary alcohol.

CH₃CHO + NaBH₄, CH₃OH → ?

CH₃CH₂OH. Aldehyde becomes primary alcohol.

CH₃COCH₃ + NaBH₄, CH₃OH → ?

CH₃CH(OH)CH₃. Ketone becomes secondary alcohol.

CH₃CH₂OH + PCC, CH₂Cl₂ → ?

CH₃CHO. Primary alcohol becomes aldehyde.

CH₃CH(OH)CH₃ + PCC → ?

CH₃COCH₃. Secondary alcohol becomes ketone.

CH₃COOCH₃ + LiAlH₄; H₃O⁺ → ?

CH₃CH₂OH + CH₃OH. Ester reduces to alcohols.

CH₃COOH + SOCl₂ → ?

CH₃COCl. Carboxylic acid becomes acid chloride.

CH₃COCl + CH₃OH → ?

CH₃COOCH₃. Acid chloride becomes ester.

CH₃COCl + NH₃ → ?

CH₃CONH₂. Acid chloride becomes amide.

CH₃COCl + CH₃SH → ?

CH₃COSCH₃. Acid chloride becomes thioester.

CH₃CONH₂ + LiAlH₄; H₃O⁺ → ?

CH₃CH₂NH₂. Amide carbonyl becomes CH₂.

CH₃CH₂Br + Mg, ether → ?

CH₃CH₂MgBr. Grignard reagent forms.

CH₃CH₂MgBr + CO₂; H₃O⁺ → ?

CH₃CH₂COOH. Carboxylic acid with one extra carbon.

CH₃MgBr + CH₃CHO; H₃O⁺ → ?

CH₃CH(OH)CH₃. Secondary alcohol forms.

CH₃MgBr + CH₃COCH₃; H₃O⁺ → ?

(CH₃)₃COH. Tertiary alcohol forms.

CH₃COOH + CH₃OH, H⁺ → ?

CH₃COOCH₃. Fischer esterification.

CH₃COOCH₃ + H₃O⁺, heat → ?

CH₃COOH + CH₃OH. Acidic ester hydrolysis.

CH₃COOCH₃ + NaOH, H₂O → ?

CH₃COO⁻Na⁺ + CH₃OH. Basic ester hydrolysis.

CH₃COOCH₃ + NaOH, then H₃O⁺ → ?

CH₃COOH + CH₃OH. Hydrolysis followed by acidification.

CH₃COCH₃ + NH₂NH₂ → ?

CH₃C(=NNH₂)CH₃. Hydrazone forms.

CH₃COCH₃ + NH₂NH₂, KOH, heat → ?

CH₃CH₂CH₃. Wolff-Kishner removes carbonyl oxygen.

CH₃COCH₃ + Zn(Hg), HCl → ?

CH₃CH₂CH₃. Clemmensen reduction removes C=O.

CH₃CHO + NH₃, mildly acidic conditions → ?

CH₃CH=NH. Imine forms, with water eliminated.

CH₃COCH₃ + pyrrolidine, H⁺ → what forms?

An enamine. A secondary amine reacts with the ketone.

CH₃COCH₃ + HCN, KCN → ?

(CH₃)₂C(OH)CN. Cyanohydrin forms.

CH₃COCH₃ + CH₂=PPh₃ → ?

(CH₃)₂C=CH₂. Wittig converts C=O into C=C.

CH₃CH₂CHO + NaOH, H₂O → reaction type?

Aldol addition. The aldehyde has alpha hydrogens.

Aldol addition product + heat → common change?

Dehydration: loses H₂O and forms C=C.

CH₃COOCH₃ + NaOCH₃, CH₃OH → reaction type?

Claisen condensation. Ester enolate attacks another ester.

CH₃COCH₃ + LDA, −78°C → what forms?

Enolate. LDA removes an alpha hydrogen.

Enolate + CH₃I → what happens?

Alpha methylation. A CH₃ group bonds to the alpha carbon.

CH₃COCH₃ + excess Br₂, NaOH → reaction type?

Haloform reaction. A methyl ketone is cleaved.

CH₃CH₂COCH₃ + excess Br₂, NaOH; H₃O⁺ → ?

CH₃CH₂COOH. Haloform reaction removes the methyl-ketone end.