Synthesis

Question 1

alkane —> chloroalkane

Answer 1

reagents: chlorine
conditions: UV light
mechanism: free radical sub
equation: CH₄ + Cl₂ ⇒ CH₃Cl + HCl (example)

Question 2

chloroalkane —> alcohol

Answer 2

reagents: aqueous NaOH
conditions: warm
mechanism: Nucleophilic sub
equation: R-Cl + NaOH ⇒ R-OH + NaCl

Question 3

Chloroalkane —> alkene

Answer 3

reagents: ethanolic KOH
conditions: warm
mechanism: elimination
equation: CH₃CH₂Cl + KOH ⇒ CH₂=CH₂ + KCl + H₂O (example)

Question 4

chloroalkane —> nitrile

Answer 4

reagents: aqueous and alcoholic KCN
conditions: heat under reflux
mechanism: Nucleophilic sub
equation: R-Cl + KCN ⇒ R-CN + KCl

Question 5

primary amine —> secondary amine —> tertiary amine —> quaternary salt

Answer 5

reagents: chloroalkane
conditions: warm
mechanism: nucleophilic substitution
equation: R₁-NH₂ + R₂-Cl ⇒ R₁R₂NH + HCl

Question 6

alkene —> alkane

Answer 6

reagents: hydrogen, Ni catalyst
conditions: 150 ^oC, high pressure
mechanism: electrophilic addition
equation: CH₂=CH₂ + H₂ ⇒ CH₃CH₃ (example)

Question 7

alkene —> dibromoalkane

Answer 7

reagents: bromine
conditions: room temperature
mechanism: electrophilic addition
equation: CH₂=CH₂ + Br₂ ⇒ CH₂BrCH₂Br (example)

Question 8

alkene —> bromoalkane

Answer 8

reagents: hydrogen bromide
conditions: room temperature
mechanism: electrophilic additon
equation: CH₂=CH₂ + HBr ⇒ CH₃CH₂Br (example)

Question 9

alkene —> alkylhydrogensulphate

Answer 9

reagents: concentrated sulphuric acid
conditions: cold
mechanism: electrophilic addition
equation: CH₂=CH₂ + H₂SO₄ ⇒ CH₃CH₂OSO₃H (example)

Question 10

alkylhydrogensulphate —> alcohol

Answer 10

reagents: water
conditions: warm
mechanism: nucleophilic sub
equation: CH₃CH₂OSO₃H + H₂O ⇒ CH₃CH₂OH + H₂SO₄ (example)

Question 11

alkene —> alcohol

Answer 11

reagents: steam
conditions: 300 ^oC, 60 atm, phosphoric acid catalyst
equation: CH₂=CH₂ +H₂O ⇒ CH₃CH₂OH

Question 12

nitrile —> primary amine

Answer 12

reagents: LiAlH₄
conditions: dry ether
equation: R-CN + 4[H] ⇒ R-CH₂NH₂ (example)

Question 13

alcohol —> alkene

Answer 13

reagents: Al₂O₃
conditions: high temperature
equation: CH₃CH₂OH ⇒ CH₂=CH₂ + H₂O (example)

Question 14

primary alcohol —> aldehyde

Answer 14

reagents: K₂Cr₂O₇ and dilute H₂SO₄
conditions: heat under reflux, distill to prevent carb formation

Question 15

secondary alcohol —> ketone

Answer 15

reagents: K₂Cr₂O₇ and dilute H₂SO₄
conditions: heat under reflux
equation: R₁R₂CHOH + [O] ⇒ R₁-COR₂ + H₂O

Question 16

primary alcohol —> carboxylic acid

Answer 16

reagents: K₂Cr₂O₇ and dilute H₂SO₄
conditions: heat, reflux
equation: R-CH₂OH + 2[O] ⇒ R-COOH + H₂O

Question 17

carbonyl —> alcohol

Answer 17

reagents: aqueous NaBH₄(aq)
conditions: room temperature
equation: R₁-COR₂ + 2[H] ⇒ R₁R₂CHOH

Question 18

carboxylic acid —> carboxylate salt

Answer 18

reagents: NaOH
conditions: room temperature
equation: R-COOH + NaOH ⇒ R-COONa + OH

Question 19

amine —> alkylammonium salt

Answer 19

reagents: haloalkane
conditions: room temperature

Question 20

carbonyl —> hydroxynitrile

Answer 20

reagents: KCN
conditions: small H₂SO₄ and room temperature
equation: R₁COR₂ + KCN ⇒ R₁R₂COHCN

NB This reaction adds an extra carbon atom and introduces an extra functional group onto the molecule

Question 21

acyl chloride —> carboxylic acid

Answer 21

reagents: water
conditions: room temperature
equation: R-COCl + H₂O ⇒ R-COOH

Question 22

acyl chloride —> amide

Answer 22

reagents: aqueous ammonia
conditions: excess
equation: R-COCl + 2NH₃ ⇒ R-CONH₂ +NH₄Cl

Question 23

acid anhydride —> carboxylic acid

Answer 23

reagents: water
conditions: warm
equation: (RCO)₂O + H₂O ⇒ 2R-COOH

Question 24

acid anhydride —> amide

Answer 24

reagents: ammonia
conditions: warm
equation: (RCO)₂O + NH₃ ⇒ R-CONH₂ + RCOOH

Question 25

carboxylic acid + alcohol —> ester (esterification)

Answer 25

reagents: concentrated sulphuric acid
conditions: heat under reflux
equation: R₁COOH + R₂OH ⇒ R₁COOR₂ + H₂O

Question 26

acyl chloride + alcohol —> ester

Answer 26

conditions: room temperature
equation: R₁COCl + R₂OH ⇒ R₁COOR₂ + HCl

Question 27

acid anhydride + alcohol —> ester

Answer 27

conditions: warm
equation: (R₁CO)₂O + R₂OH ⇒ R₁COOR₂ + R₁COOH

Question 28

ester —> carboxylic acid + alcohol

Answer 28

reagents: dilute sulphuric acid
conditions: heat under reflux
equation: R₁COOR₂ + H₂O ⇒ R₁COOH + R₂OH

Question 29

ester —> carboxylate salt + alcohol

Answer 29

reagents: NaOH(aq)
conditions: heat under reflux
equation: R₁COOR₂ + NaOH ⇒ R₁COONa + R₂OH

Question 30

acyl chloride + primary amine —> N-substituted amide

Answer 30

conditions: room temperature
equation: R₁-COCl + 2R₂-NH₂ ⇒ R₁-CONHR₂ + R₂-NH₃Cl

Question 31

acid anhydride + primary amine —> N-substituted amide

Answer 31

conditions: warm
equation: (R₁CO)₂O+ R₂-NH₂ ⇒ R₁-CONHR₂ + R₁-COOH

Question 32

benzene —> nitrobenzene

Answer 32

eagents: concsulphuric and nitric acids
conditions: below 55•c and reflux
equation: C₆H₆ + HNO₃ ⇒ C₆H₅NO₂ + H₂O

Question 33

benzene —> alkylbenzene

Answer 33

reagents: chloroalkane, AlCl₃
conditions: 50•c and reflux
equation: C₆H₆ + RCl ⇒ C₆H₅R + HCl

Question 34

benzene —> phenylketone

Answer 34

reagents: acyl chloride, AlCl₃
conditions: room temperature and non-dry environment
equation: C₆H₆ + RCOCl ⇒ C₆H₅COR + HCl

Question 35

nitrobenzene —> phenylamine

Answer 35

reagents: tin, concentrated HCl
conditions: reflux
equation: C₆H₆ + 6[H] ⇒ C₆H₅NH₂ + 2H₂O

Question 36

Phenylamine —> N-phenylethanamide

Answer 36

reagents: ethanol chloride
conditions: reflux (Addition-elimination)

Question 37

chloroalkane —> 1 amine

Answer 37

reagents: ethanolic NH₃
conditions: Excess
mechanism: nuc sub
equation: CH₃Cl + 2NH₃ ⇒ CH₃NH₂ + NH₄⁺