Reactions in Topic XI

X2
1. Alkane   Haloalkane X2: Br2 or Cl2
UV light or heat

X2 (in organic solvent)

2. Alkene  Haloalkane X2: Cl2, Br2, I2

H2 , Pt
3. Alkene   Alkane

HX
4. Alkene   Haloalkane HX: HF, HBr, HCl, HI
(Prediction of major product by Markovnikov’s
Rule)

NaOH(aq)
5. Haloalkane  Alcohol

HX or PX3
6. Alcohol   Haloalkane HX: HCl, HBr, HI
PX3: PCl3, PBr3, PI3

Al2O3 , heat
7. Alcohol   Alkene
or conc. H2 SO4 , heat

Cr2O72(aq) / H+(aq)
8. 1 Alcohol   Aldehyde
heat
or Carboxylic acid

Cr2O72(aq) / H+(aq)
9. 2 Alcohol   Ketone
heat

1. LiAlH4 , dry ether

10. Ketone or Aldehyde   Alcohol
2. H+(aq)
NaBH4
Ketone or Aldehyde   Alcohol
H2O

Cr2O72(aq) / H+(aq)
11. Aldehyde   Carboxylic acid
heat
 conc. H2 SO4 , heat
12. Carboxylic acid + Alcohol Ester + Water

1. LiAlH4 , dry ether

13. Carboxylic acid   Alcohol
2. H+(aq)

1. PCl3
14. Carboxylic acid  Unsubstituted amide
2. NH3

1. OH(aq), heat
15. Ester   Carboxylic acid + Alcohol
2. H+(aq)
H(aq), heat
Ester Carboxylic acid + Alcohol

1. OH(aq), heat
16. Amide   Carboxylic acid + Alkylammonium salt
2. H+(aq)

H(aq), heat
Amide   Carboxylic acid + Alkylammonium salt
Inter-conversions between the functional groups

Ester Amide
O O
║ ║
R–C–OR’ R–C–NH2

Carboxylic acid
O
║
R–C–OH

Cr2O72-(aq)/H+(aq), 

Cr2O72-(aq)/H+(aq),  Aldehyde
1
H2, Pt Alkene Al2O3,  Alcohol 1. LiAlH4, dry ether O
2. H+(aq)
(CnH2n) or conc. (ROH) or ║
H2SO4,  2 NaBH4, water
R–C–H
X2 (in
organic
solvent)
or
HX
Ketone
Alkane X2 Haloalkane O
(CnH2n+2) UV light (RX) ║
or 
R–C–R’