Back to AI Flashcard MakerChemistry /OCR A-Level Chemistry: Chapter 28 - Organic Synthesis

OCR A-Level Chemistry: Chapter 28 - Organic Synthesis

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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

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Key Terms

Term
Definition

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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TermDefinition

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


RCH2CN -> RCH2CH2NH2

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
Heated under reflux woth aqueous hydroxide ions
Broken down by water into products

R-CHO -> R-COOH

Aldehyde to carboxylic acid

K2Cr2O7 / H2SO4
Strong heat
Under reflux
Oxidation

R-CH=CH2 -> RCH2CH2OH

Alkene to primary alcohol

H3PO4 / H2O(g)

Hydration

R-CH2OH -> R-CHO

Primary alcohol to aldehyde

K2Cr2O7 / H2SO4
Gentle heating
Distill off
Oxidation

RCH2Br -> RCH2NH2

Haloalkane to primary amine


Haloalkane + NH3 (xs)
Salt + NaOH -> primary amine
Ethanol as solvent


R’COCl -> R’COOCH2R

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
50°C
Nitration

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
Room temp
No catalyst
Bromination

Alkene to alkane

H2/Ni

| 423K

Secondary alcohol to ketone

K2Cr2O7/H2SO4

| Heated under reflux

Primary amine to secondary amine

Primary amine + CH3Br
Ethanol as solvent
Salt product + NaOH forms amine

Amino acid to ester

Alcohol + amino acid
H2SO4
NaOH

Two monomers to polyamide

Dioic acid

| Diamide

One monomer to poly amide

Amino acid

Two monomers to polyester

Diol

| Dicarboxylic acid