Reactions

Question 1

Free radical sub?

Answer 1

Cl2, UV, heat

-limited Cl2/excess alkane

Question 2

Alkene to alkane?

Answer 2

@reduction

• H2(g), Pt, rtp
• H2(g), Ni, heat

Question 3

H-X to alkene

Answer 3

@elimination

-KOH in ethanol, reflux

Question 4

Alkene to alcohol

Answer 4

@E.A

-industrial: H20(steam), H3PO4 cat., heat, high pressure

• lab
  1. Cold H2SO4
  2. Heat, H2O

Question 5

Alcohol to Alkene

Answer 5

@elimination

• industrial: Al2O3, heat
• c H2SO4, reflux

Question 6

Alkene to HX

Answer 6

@E.A

1. Conc HX
2. HX(aq) in CCl4
3. HCl(g) generated in Situ

Question 7

Alkene to xx

Answer 7

@E.A

-X2 in CCl4, rtp, dark

Question 8

Alkene to X,OH

Answer 8

@E.A

-X2(aq), rtp, dark

-aq: OH acts a nucleophile
=> major pdt

Question 9

Alkene to diol

Answer 9

@oxidation
*cold

• KMnO4, H2SO4(aq)
• KMnO4, NaOH(aq)

Question 10

Alkene to

1. Carboxylic acid
2. Ketone
3. CO2 + H2O

Answer 10

@oxidative cleavage

-KMnO4, H2SO4, reflux

TERMINAL only

Question 11

Alcohol to ester

Answer 11

@condensation
-+COOH, c H2SO4, reflux

@N.S
CH3COCl, anhyd., rtp

Question 12

Alcohol to RX

Answer 12

@N.S

1. PCl5(s), anhydrous, rtp
2. PCl3(l)/ PBr3(l), anhydrous, rtp
3. SOCl2(l)/ SOBr2(l), anhydrous, rtp
4. conc HCl, ZnCl2/ c HBr
5. HCl(g)/HBr(g) in Situ, NaX(s) + c H2SO4

Question 13

RX to alcohol

Answer 13

@N.S

-NaOH(aq), reflux

Question 14

RX to nitrile (CN)

Answer 14

@N.S

-NaCN in ethanol, reflux

Question 15

Nitrile to increase 4H?

Answer 15

@reduction

1. LiAlH4 in dry ether, rtp
2. H2(g) and w nickel, heat
3. H2(g) with Pt., rtp

Question 16

RCN to alcohol

Answer 16

@hydrolysis

Question 17

RX to ROCH3

Answer 17

@N.S

-CH3ONa, reflux methanol solution

Question 18

RX to Amine (RNH2)

Answer 18

@N.S

• NH3, ethanolic medium, heat is sealed tube
• further substitution in excess to px 4’ salt

Question 19

Nitrile to -COOH

Answer 19

@hydrolysis

-acid catalysed: heat under reflux with dul.H2SO4

+NH4+

Question 20

Nitrile to COO-

Answer 20

@hydrolysis

-base catalysed: heat under reflux with NaOH(aq)

+NH3

Question 21

Pri alcohol -> aldehyde

Answer 21

@oxidation

K2Cr2O7(aq), H2SO4(aq), immediate distillation

Question 22

methanol to CO2+H20

Answer 22

@oxidation

KMnO4(aq), H2SO4(aq), reflux

Question 23

Tri-iodomethane test 
       OH
        |
(R)-C-CH3
        |
       H

Answer 23

@oxidation

I2(aq), NaOH(aq), reflux

Question 24

Esters, amides, acid chlorides

-> carboxylic acid

Answer 24

1. Ester
   - HCl(aq), heat
2. Amides
   - NaOH(aq), heat
3. Acid chloride
   - no need heat

Question 25

Carboxylic acid to Pri alcohol

Answer 25

@reduction

LiAlH4 in dry ether, rtp

Question 26

Carboxylic acid to acyl chloride

Answer 26

PCl5(s), PCl3(l), SOCl2(l), anhyd, rtp

Question 27

Sec alcohol to aldehyde

Answer 27

@oxidation

• K2Cr2O7, dilute H2SO4, heat under reflux
• KMnO4, H2SO4, reflux

Question 28

Aldehyde and ketone to hydroxynitriles

Answer 28

@N.A

HCN,

Small amt of NaOH(aq)/NaCN(s), cold

Question 29

Sec alcohol to ketone

Answer 29

• K2Cr2O7, d.H2SO4, reflux

* KMnO4, d.H2SO4, reflux

Question 30

Aldehyde to Pri alcohol

Answer 30

@reduction

• H2(g), Ni, heat
• H2(g), Pt, rtp
• LiAlH4 in dry ether, rtp
• NaBH4 in methanol, rtp

Question 31

Ketone to Sec alcohol

Answer 31

@reduction

• H2(g), Ni, heat
• H2(g), Pt, rtp
• LiAlH4 in dry ether, rtp
• NaBH4 in methanol, rtp

Question 32

Methanoic and ethandiotic acid to CO2 and water

Answer 32

@oxidation

KMnO4(aq), H2SO4

Question 33

Carboxylic acid to O-Na+

Answer 33

@redox

Na(s), rtp

Question 34

Carboxylic acid to

O-Na+ + H20

Answer 34

@acid base

• NaOH(aq), rtp
• Na2CO3(s)/(aq), rtp
• NaHCO3(s)/(aq), rtp

Question 35

Carboxylic acid to

 O
  II   R-C-X

Answer 35

@N.S

• anhyd PCl5(s), rtp
• anhyd PCl3(l)/PBr3(l), rtp
• anhyd SOCl2(l)/ SOBr2(l), rtp

Question 36

Ester to carboxylic acid

Answer 36

@hydrolysis, N.S

• HCl(aq)/ H2SO4(aq)/ HNO3(aq), reflux
• NaOH(aq), reflux

Question 37

Ester to Pri alcohol

Answer 37

@reduction

LiAlH4 in dry ether, rtp

Question 38

Acid chloride to carboxylic acid

Answer 38

@hydrolysis, N.S

H2O(l), rtp

+HCl

Question 39

Acid chloride to ester

Answer 39

@condensation, N.S

1. CH3CH2OH, Anhyd, rtp
2. Involving phenol:
   •NaOH(aq) or pyridine
   •fb CH3COCl, anhyd condition

Question 40

Acid chloride to amides

Answer 40

@condensation, N.S

• cNH3, rtp
• cCH3NH3, rtp
• c(CH3)2NH, rtp

Question 41

Nitrogenous cmpd to carboxylic acid

Answer 41

@hydrolysis

1. Acidic medium (-COOH)
   •HCl(aq)/ H2SO4(aq)/ HNO3(aq), reflux
2. Alkaline medium (-COO-)
   •NaOH(aq), reflux

Question 42

Nitrogenous cmpd to amines

Answer 42

@reduction

• LiAlH4 in dry ether, rtp
• H2(g), Ni(s), heat
• H2(g), Pt(s), rtp

Question 43

Nitrobenzene to phenyl amine

Answer 43

@reduction

• Sn(s), cHCl, reflux
• fb NaOH(aq)

Question 44

Amines to R-N+-H3

Answer 44

@acid-base, neutralisation

HCl(aq), H2SO4(aq), HNO3(aq), rtp

Question 45

Amines to ester

Answer 45

@condensation, N.S

CH3COCl, anhyd, rtp

Question 46

Amides to amines

Answer 46

@reduction

• LiAlH4 in dry ether, rtp
• H2(g), Ni(s), heat
• H2(g), Pt(s), rtp

Question 47

Amines to carboxylic acid

Answer 47

@acid catalysed hydrolysis

d. HCl(aq), H2SO4(aq), HNO3(aq), reflux

Question 48

Amines to carboxylate salt

Answer 48

@alkaline catalysed hydrolysis

NaOH(aq), reflux

Question 49

What’s the difference bt HCl (aq) in

1. cold
2. hot

Answer 49

cold: acid base
hot: hydrolysis

Question 50

Thermal cracking?

Answer 50

High temp (~900)

High temp (~500) w catalyst

Question 51

CH3CH2OH + PCl5 ->?

Answer 51

CH3CH2Cl + POCl3 + HCl

Question 52

3CH3CH2OH + PCl3 ->?

Answer 52

3CH3CH2Cl + H3PO3

Question 53

CH3CH2OH + SOCl2 ->?

Answer 53

CH3CH2Cl + SO2 + HCl