OCR A-Level Chemistry: Chapter 28 - Organic Synthesis
This flashcard set summarizes key organic transformations including nucleophilic addition to aldehydes, dehydration of alcohols, conversion of acyl chlorides to amides, and electrophilic addition to alkenes. Each reaction includes reagents and conditions for clarity.
R-CHO -> R-CH(OH)CN
Aldehyde to hydroxynitrile
NaCN / H+
Nucleophilic addition
Key Terms
R-CHO -> R-CH(OH)CN
Aldehyde to hydroxynitrile
NaCN / H+
Nucleophilic addition
RCH2CH2OH -> RCH=CH2
Primary alcohol to alkene
H2SO4 or H3PO4
Heated under reflux
RCOCl -> RCONH2
Acyl chloride to amide
NH3
CH2=CH2 -> CH3CH2Br
Alkene to haloalkane
Hydrogen Halide
Rapid addition
Room temperature
RCH2OH -> RCH2Br
Primary alcohol to haloalkane
Sodium halide
H2SO4
Heated under reflux
Hydrogen halide formed in situ
R’COOCH2R -> RCH2OH + R’COOH
Ester to alcohol and carboxylic acid
Dilute acid hydrolysis
Heated under reflux with dilute aqeuous acid
Broken down by water into two products
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| Term | Definition |
|---|---|
R-CHO -> R-CH(OH)CN Aldehyde to hydroxynitrile |
Nucleophilic addition |
RCH2CH2OH -> RCH=CH2 Primary alcohol to alkene | H2SO4 or H3PO4 Heated under reflux |
RCOCl -> RCONH2 Acyl chloride to amide | NH3 |
CH2=CH2 -> CH3CH2Br Alkene to haloalkane | Hydrogen Halide |
RCH2OH -> RCH2Br Primary alcohol to haloalkane | Sodium halide |
R’COOCH2R -> RCH2OH + R’COOH Ester to alcohol and carboxylic acid | Dilute acid hydrolysis |
Nitrile to amine | H2 / Ni Reduction |
RCOOH -> RCOCl Carboxylic acid to acyl chloride | SOCl2 |
RCH2Br -> RCH2OH Haloalkane to primary alcohol | NaOH(aq) Heat under reflux |
RCH2Br -> RCH2CN Haloalkane to nitrile | NaCN In ethanol |
RCH2OH + R’COOH -> R’COOCH2R + H2O Alcohol and carboxylic acid to ester and water | H2SO4 concentrated Esterification |
RCH2CN -> RCH2COOH Nitrile to carboxylic acid | H2O / HCl Hydrolysis |
R’COOCH2R -> RCH2OH + R’COO- Na+ Ester to alcohol and sodium salt of carboxylic acid | Alkaline hydrolysis |
R-CHO -> R-COOH Aldehyde to carboxylic acid | K2Cr2O7 / H2SO4 |
R-CH=CH2 -> RCH2CH2OH Alkene to primary alcohol | H3PO4 / H2O(g) Hydration |
R-CH2OH -> R-CHO Primary alcohol to aldehyde | K2Cr2O7 / H2SO4 |
RCH2Br -> RCH2NH2 Haloalkane to primary amine |
|
Acyl chloride to ester | Alcohol |
RCOCl -> RCOOH Acyl chloride to carboxylic acid | H2O |
RCOCl -> RCONHR’ Acyl chloride to secondary amide | R’NH2 Primary amine |
R-CHO -> R-CH2OH Aldehyde to primary alcohol | NaBH4 / H2O Reduction |
Benzene to methylbenzene | CH3Cl/FeCl3 Alkylation |
Benzene to phenylethanone | CH3CClO/FeCl3 Acylation |
Phenylethanone to phenylethanol | NaBH4 Reduction |
Benzene to chlorobenzene | Cl2/AlCl3 | Chlorination |
Benzene to bromobenzene | Br2/AlBr3 | Bromination |
Benzene to nitrobenzene | HNO3/H2SO4 |
Nitrobenzene to phenylamine | Sn/HCl Heated under reflux Forms ammonium salt Ammonium salt reacts with NaOH Phenylamine produced Reduction |
Phenylamine to tribromophenylamine | Br2 |
Phenol to 2-nitrophenol/4-nitrophenol | HNO3 | Nitration |
Phenol to sodium salt of phenol | NaOH | Neutralisation |
Phenol to tribromophenol | Br2 |
Alkene to alkane | H2/Ni | 423K |
Secondary alcohol to ketone | K2Cr2O7/H2SO4 | Heated under reflux |
Primary amine to secondary amine | Primary amine + CH3Br |
Amino acid to ester | Alcohol + amino acid |
Two monomers to polyamide | Dioic acid | Diamide |
One monomer to poly amide | Amino acid |
Two monomers to polyester | Diol | Dicarboxylic acid |