Organic Mechanisms

Question 1

Alkane to Haloalkane

Answer 1

Mechanism: Free Radical Substitution
Reagent: Halogen
Condition: UV light

Question 2

Haloalkane to Alcohol

Answer 2

Mechanism: Nucleophilic Substitution
Reagent: NaOH
Conditions: Warm, aqueous, reflux

Question 3

Haloalkane to Nitrile

Answer 3

Mechanism: Nucleophilic Substitution
Reagent: KCN
Conditions: Hot (reflux), ethanolic

Question 4

Haloalkane to Amine

Answer 4

Mechanism: Nucleophilic Substitution
Reagent: NH3
Condition: Heat (warm), XS NH3

Question 5

Haloalkane to Alkene

Answer 5

Mechanism: Elimination
Reagent: NaOH
Condition: Ethanolic, reflux

Question 6

Alkene to Haloalkane

Answer 6

Mechanism: Electrophilic Addition
Reagent: Halogen (e.g. Cl2 or Br2)
Condition: Aqueous

OR

Reagent: HX (hydrogen halide)
Condition: Room temp (approx. 25 degrees Celsius)

Question 7

Alkene to Alcohol

Answer 7

Mechanism: Hydration
Reagent: H3PO4 catalyst
Condition: Steam, 300 degrees Celsius, 60 atm

Question 8

Alcohol to Alkene

Answer 8

Mechanism: Elimination
Reagent: XS conc. H2SO4
Condition: 170 degrees Celsius

Question 9

Alcohol to Aldehyde

Answer 9

Mechanism: Oxidation
Reagent: K2Cr2O7, H2SO4
Condition: Heat primary alcohol in distillation apparatus

Question 10

Alcohol to Ketone

Answer 10

Mechanism: Oxidation
Reagent: K2Cr2O7, H2SO4
Condition: Heat secondary alcohol under reflux

Question 11

Aldehyde to Alcohol

Answer 11

Mechanism: Reduction (nucleophilic addition)
Reagent: NaBH4
Condition: Aqueous, in water with methanol

Question 12

Ketone to Alcohol

Answer 12

Mechanism: Reduction (nucleophilic addition)
Reagent: NaBH4
Condition: Aqueous, in water with methanol

Question 13

Aldehyde/Ketone to 2-hydroxynitrile

Answer 13

Mechanism: Nucleophilic Addition
Reagent: KCN followed by dilute acid (e.g. H2SO4)
Condition: Aqueous, room temp (approx. 25 degrees Celsius)

Question 14

Aldehyde to Carboxylic Acid

Answer 14

Mechanism: Oxidation
Reagent: K2Cr2O7, H2SO4
Condition: Reflux

Question 15

Acyl Chloride to Carboxylic Acid

Answer 15

Mechanism: Nucleophilic Addition-Elimination
Reagent: H2O
Condition: Room temp

Question 16

Acyl Chloride to Ester

Answer 16

Mechanism: Nucleophilic Addition-Elimination
Reagent: Alcohol, conc H2SO4
Condition: Room temp

Question 17

Acyl Chloride to Amide

Answer 17

Mechanism: Nucleophilic Addition- Elimination
Reagent: NH3
Condition: Room temp

Question 18

Acyl Chloride to N-substituted amide

Answer 18

Mechanism: Nucleophilic Addition- Elimination
Reagent: Amine
Condition: Room temp

Question 19

Carboxylic Acid to Ester

Answer 19

Mechanism: Esterification
Reagent: Alcohol, conc. H2SO4 catalyst
Condition: Reflux

Question 20

Ester to Carboxylic Acid

Answer 20

Mechanism: Hydrolysis
Reagent: Dilute acid (e.g. HS2O4), H2O
Condition: Reflux

Question 21

Benzene to Cyclohexane

Answer 21

Mechanism: Hydrogenation
Reagent: H2
Condition: Ni catalyst, 200 degrees Celsius

Question 22

Benzene to Nitrobenzene

Answer 22

Mechanism: Electrophilic Substitution
Reagent: Conc. HNO3 and conc. H2SO4
Condition: Below 55 degrees Celsius

Question 23

Nitrobenzene to Phenylamine

Answer 23

Mechanism: Reduction
Reagent: Sn/HCl
Condition: Reflux/heat

Question 24

Phenylamine to N-phenylethanamide

Answer 24

Mechanism: Nucleophilic Addition-Elimination
Reagent: CH3COCl
Condition: Room temp

Question 25

Benzene to Phenylketone

Answer 25

Mechanism: Electrophilic Substitution Reagent: RCOCl, AlCl3 catalyst Condition: Reflux, anhydrous environment

Question 26

Alcohol to Haloalkane

Answer 26

Mechanism: Nucleophilic Substitution Reagent: NaX, H2SO4 Condition: Room temp

Question 27

Alkene to Alkane

Answer 27

Mechanism: Hydrogenation Reagent: H2 Condition: Ni catalyst, 200 degrees Celsius

Question 28

Nitrile to Primary Amine

Answer 28

Mechanism: Reduction Reagent: LiAlH4 Condition: Dilute H2SO4