Paper 2 - All Memorizations

1) Alkane → Halogenoalkane

Reagent: Halogen₂

Conditions: UV Light

Mechanism: Free-radical Substitution

2) Alkene → Halogenoalkane

Reagents: HX

Mechanism: Electrophilic Addition

3) Alkene → Dihaloalkane

Reagents: Halogen₂

Mechanism: Electrophilic Addition

4) Alkene → Alcohol

Reagents: H₂O

Conditions: Conc. H₂SO₄, 300^o C, 7 MPa

Mechanism: Electrophilic Addition

5) 1^o Halogenoalkane → 1^o Amine

Reagents: Conc. NH₃

Conditions: Excess NH₃ dissolved in ethanol

Mechanism: Nucleophilic Substitution

6) 1^o Halogenoalkane → 2^o Amine

Reagents: 1^o Amine

Conditions: Amine dissolved in ethanol

Mechanism: Nucleophilic Substitution

7) 1^o Halogenoalkane → 1^o Alcohol

Reagents: NaOH (aq)

Conditions: Heat under reflux

Mechanism: Nucleophilic Substitution

8) 2^o Halogenoalkane → 2^o Alchol

Reagents: NaOH (aq)

Conditions: Heat under reflux

Mechanism: Nucleophilic Substitution

9) 3^o Halogenoalkane → 3^o Alcohol

Reagents: NaOH (aq)

Conditions: Heat under reflux

Mechanism: Nucleophilic Substitution

10) 1^o/2^o/3^o Halogenoalkane → Alkene

Reagents: KOH (dissolved in ethanol)

Conditions: Heat under reflux

Mechanism: Elimination

11) 1^o Halogenoalkane → Nitrile

Reagents: KCN (dissolved in ethanol)

Mechanism: Nucleophilic Substitution

12) Alcohol → Alkene

Reagents: Conc. H₂SO₄/Conc. H₃PO₄/Al₂O₃ catalyst

Conditions: 170^o C for acid dehydration

Mechanism: Elimination

13) Alcohol → Halogenoalkane

Reagents: HX (prepared in situ from NaX and conc. H₂SO₄

Conditions: Heat under reflux

14) 1^o Alcohol → Aldehyde

Reagents: Acidified K₂Cr₂O₇

Conditions: Heat and distil

15) 2^o Alcohol → Ketone

Reagents: Acidified K₂Cr₂O₇

Conditions: Heat under reflux

16) Aldehyde → Carboxylic Acid

Reagents: Acidified K₂Cr₂O₇

Conditions: Heat under reflux

17) Aldehyde → 1^o Alcohol

Reagents: NaBH₄

Conditions: Aqueous solution

Mechanism: Nucleophilic Addition

18) Ketone → 2^o Alcohol

Reagents: NaBH₄

Conditions: Aqueous solution

Mechanism: Nucleophilic Addition

19) Aldehyde/Ketone → Hydroxynitrile

Reagents: KCN followed by dilute acid

Mechanism: Nucleophilic Addition

20) Carboxylic Acid → Aldehyde

Reagents: LiAlH₄

Conditions: In dry ether

Mechanism: Nucleophilic addition

21) Carboxylic Acid → 1^o Alcohol

Reagents: LiAlH₄

Conditions: In dry ether

Mechanism: Nucleophilic Addition

22) Carboxylic Acid → Ester

Reagents: Alcohol

Conditions: Conc. H₂SO₄

Mechanism: Nucleophilic Addition-Elimination

23) Nitrile → 1^o Amine

Reagents: LiAlH₄

Conditions: In dry ether

Mechanism: Nucleophilic Addition

24) Carboxylic Acid → Ammonium Salt

Reagents: Ammonia solution

Conditions: Room temperature

25) Carboxylic Acid → Sodium Salt

Reagents: NaOH (aq), Na₂CO₃

Conditions: Room temperature

26) Acid Chloride → Carboxylic Acid

Reagents: H₂O

Conditions: Room temperature

Mechanism: Nucleophilic Addition-Elimination

27) Acid Chloride → Amide

Reagents: Ammonia

Conditions: Acid chloride added to conc ammonia

Mechanism: Nucleophilic Addition-Elimination

28) Acid Chloride → Ester

Reagents: Alcohol added to acid chloride

Conditions: Room temperature

Mechanism: Nucleophilic Addition-Elimination

29) Ester → Carboxylic Acid

Reagents: Dilute HCl

Conditions: Heat under reflux

30) Ester → Salt of Carboxylic Acid

Reagents: NaOH solution

Conditions: Heat under reflux

31) Acid Anhydride → Carboxylic Acid

Reagents: H₂O

Conditions: Room temperature

32) Acid Anhydride → Amide

Reagents: Conc NH₃

Conditions: Room temperature

33) Acid Anhydride → Ester

Reagents: Alcohol

Conditions: Room temperature

34) Benzene → Nitrobenzene

Reagents: Conc HNO₃, Conc H₂SO₄

Conditions: Low temp to prevent further nitration

Mechanism: Electrophilic Substitution

35) Nitrobenzene → Phenylamine

Reagents: Sn, HCl

Conditions: Heat under reflux + add NaOH (aq) to liberate free amine

36) Benzene → Phenylethanone

Reagents: CH₃COCl or (CH₃CO)₂O

Conditions: AlCl₃ catalyst w/ CH₃COCl

Mechanism: Electrophilic Substitution

Test for alcohols

K₂Cr₂O₇ oxidises 1^o + 2^o, not 3^o

• Will turn orange to green

1^o oxidises to aldehyde

2^o oxidises to ketone

Tests for aldehydes + ketones

1) Fehling’s solution

Oxidises aldehydes, not ketones

Add warm to sample - if changes to brick red, aldehyde present

2) Tollens’s reagent (NaOH to AgNO₃)

Add warm to sample - if reduced to silver mirror, aldehyde present

Test for alkenes

Bromine water will decolourise in unsaturated compounds

Test for carboxylic acids

Add sodium hydrogen carbonate (NaHCO₃) to sample - if present, CO₂ gas/effervescence will show