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Questions and Answers
What is the product of the reduction of a nitrile using LiAlH4 in dry ether?
amine
N.S.- PBr3, Heat - SOCl2, Heat - HCl(g), Heat - ___
PCl5
What compound is formed when a primary alcohol is oxidized using K2Cr2O7(aq) and H2SO4(aq)?
What reagent is used for the reduction of aldehydes and ketones?
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Match the following carbonyl compound with the correct oxidation method:
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Amine RNH2 can be converted to a secondary amine RNHR' through a process involving _.
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Study Notes
Aliphatic Compounds
Alkanes
- Combustion reactions: CO2 + H2O with excess O2, CO + H2O with limited O2
- Reduction reactions: H2, Pt/Pd, H2, Ni, Heat
- Elimination reactions: KOH(alc)/NaOH (alc), Heat
Alkenes
- Characterized by the presence of a C=C bond
- Unknown properties (q)
Halogenoalkanes
- General formula: RX
- Nucleophilic Substitution (N.S.) reactions: NaOH, Heat; PBr3, Heat; SOCl2, Heat; HCl(g), Heat; PCl5
- Electrophilic Addition (E.A.) reactions: Br2 in CCl4, resulting in a color change from orange to colorless
- Hydrogen halide gas reactions: HBr(g)
- Reaction with RONa and EtOH: forms Nats
Alcohols
- General formula: ROH
- Elimination reactions: Excess conc. H2SO4, Heat or Al2O3, Heat
- Oxidative cleavage reactions: KMnO4(aq), H2SO4(aq), Heat
- Condensation reactions: RCO2H, ROH, H2SO4(aq), Heat
- Reduction reactions: LiAlH4, in dry ether
- Oxidation reactions: K2Cr2O7(aq), H2SO4(aq), Heat; KMnO4(aq)
- Primary (1°) alcohol oxidation: forms RCHO
- Secondary (2°) alcohol oxidation: forms RCOR
Nitriles
- General formula: RCN
- Nucleophilic Substitution (N.S.) reactions: KCN(alc), Heat; 1° RNH2, excess NH3, Heat in a sealed tube
- Reduction reactions: LiAlH4, in dry ether
Amines
- General formula: RNH2
- Reaction with 2° RNHR': forms R3N, Heat
- Reaction with HCN(aq): requires trace NaOH(aq)
- Hydrolysis reactions: H2SO4(aq), Heat
- Reduction reactions: LiAlH4, in dry ether
Carbonyls
- General formula: CHO/COC
- Oxidation reactions: KMnO4(aq), H2SO4(aq), Heat; K2Cr2O7(aq)
- Iodoform reaction: I2(aq) in NaOH, Warm, then dilute H2SO4
Carboxylic Acids
- General formula: RCO2H
- Hydrolysis/Nucleophilic Substitution (N.S.) reactions: H2O
- Decarboxylation reactions: Na/NaOH/NaHCO3/Na2CO3, Soda lime, Heat
Alkane Sodium Salt
- General formula: RCO2Na
- Hydrolysis reactions: HCl(aq), H2SO4(aq), NaOH(aq), Heat
- Nucleophilic Substitution (N.S.) reactions: NH3/RNH2
Alkyl Chloride
- General formula: RCOCl
- Nucleophilic Substitution (N.S.) reactions: PCl5, SOCl2, Heat, PC13, Heat
Amides
- General formula: RCONH2
Free Radical Substitution
- Initiation reaction: Cl2 -> 2Cl
- Propagation reaction: CH3CH2
Aliphatic Compounds
Alkanes
- Combustion reactions: CO2 + H2O with excess O2, CO + H2O with limited O2
- Reduction reactions: H2, Pt/Pd, H2, Ni, Heat
- Elimination reactions: KOH(alc)/NaOH (alc), Heat
Alkenes
- Characterized by the presence of a C=C bond
- Unknown properties (q)
Halogenoalkanes
- General formula: RX
- Nucleophilic Substitution (N.S.) reactions: NaOH, Heat; PBr3, Heat; SOCl2, Heat; HCl(g), Heat; PCl5
- Electrophilic Addition (E.A.) reactions: Br2 in CCl4, resulting in a color change from orange to colorless
- Hydrogen halide gas reactions: HBr(g)
- Reaction with RONa and EtOH: forms Nats
Alcohols
- General formula: ROH
- Elimination reactions: Excess conc. H2SO4, Heat or Al2O3, Heat
- Oxidative cleavage reactions: KMnO4(aq), H2SO4(aq), Heat
- Condensation reactions: RCO2H, ROH, H2SO4(aq), Heat
- Reduction reactions: LiAlH4, in dry ether
- Oxidation reactions: K2Cr2O7(aq), H2SO4(aq), Heat; KMnO4(aq)
- Primary (1°) alcohol oxidation: forms RCHO
- Secondary (2°) alcohol oxidation: forms RCOR
Nitriles
- General formula: RCN
- Nucleophilic Substitution (N.S.) reactions: KCN(alc), Heat; 1° RNH2, excess NH3, Heat in a sealed tube
- Reduction reactions: LiAlH4, in dry ether
Amines
- General formula: RNH2
- Reaction with 2° RNHR': forms R3N, Heat
- Reaction with HCN(aq): requires trace NaOH(aq)
- Hydrolysis reactions: H2SO4(aq), Heat
- Reduction reactions: LiAlH4, in dry ether
Carbonyls
- General formula: CHO/COC
- Oxidation reactions: KMnO4(aq), H2SO4(aq), Heat; K2Cr2O7(aq)
- Iodoform reaction: I2(aq) in NaOH, Warm, then dilute H2SO4
Carboxylic Acids
- General formula: RCO2H
- Hydrolysis/Nucleophilic Substitution (N.S.) reactions: H2O
- Decarboxylation reactions: Na/NaOH/NaHCO3/Na2CO3, Soda lime, Heat
Alkane Sodium Salt
- General formula: RCO2Na
- Hydrolysis reactions: HCl(aq), H2SO4(aq), NaOH(aq), Heat
- Nucleophilic Substitution (N.S.) reactions: NH3/RNH2
Alkyl Chloride
- General formula: RCOCl
- Nucleophilic Substitution (N.S.) reactions: PCl5, SOCl2, Heat, PC13, Heat
Amides
- General formula: RCONH2
Free Radical Substitution
- Initiation reaction: Cl2 -> 2Cl
- Propagation reaction: CH3CH2
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Description
Test your knowledge of aliphatic compounds, including alkanes, alkenes, halogenoalkanes, and alcohols, and their reactions including combustion, reduction, elimination, and more.
