Aliphatic Organic Synthesis

Question 1

Alkane Complete Combustion

Answer 1

C₅H₁₂ + 8O₂ →5CO₂ + 6H₂O

Question 2

Alkane Incomplete Combustion

Answer 2

C₅H₁₂ + 3O₂ → 5C + 6H₂O

Question 3

Alkane to Halogenoalkane

Answer 3

Free Radical Substitution
Using UV light
Initiation
Propagation
Termination

Question 4

Initiation Step

Answer 4

Cl₂ → 2Cl

Question 5

Propagation Step

Answer 5

CH₄ + Cl →CH₃ +HCl
CH₃ + Cl₂ → CH₃Cl + Cl

Question 6

Termination Step

Answer 6

Cl + Cl →Cl₂
CH₃ + Cl → CH₃Cl
CH₃ + CH₃ → C₂H₆

Question 7

Alkene to Dihalogenoalkane

Answer 7

Use Pure Br2
C2H4 + Br2 → C2H4Br2

Question 8

Alkene to Alkane

Answer 8

150 degree C + Nickel Catalyst
C2H4 + H2 → C2H6

Question 9

Alkene to Halogenoalkane

Answer 9

Use HBr
C2H4 + HBr → C2H5Br

Question 10

Alkene to Alcohol

Answer 10

Use Heat + H3PO4 + Steam
C2H4 + H2O → C2H5OH

Question 11

Alkene to Diol

Answer 11

Use KMnO4 + Acidic Conditions + Cold Temperature
C2H4 + [O] → CH2(OH)CH2(OH)

Question 12

Aldehyde Reduction

Answer 12

Use LiAlH4 + Dry Ether
RCOH + [H] → RCH2OH

Question 13

Ketone Reduction

Answer 13

Use LiAlH4 + Dry Ether
RCOR +[H] → RCH(OH)R

Question 14

Carbonyls to Hydroxynitriles

Answer 14

Use KCN in H2SO4
RCOR + KCN → CH3C(OH)(R)CN

Question 15

Acid Hydrolysis of Esters

Answer 15

Use Strong Acid
RCOOR → RCOOH + ROH

Question 16

Alkaline Hydrolysis of Esters

Answer 16

Use Strong Alkaline
RCOOR → RCOO- + ROH

Question 17

Alcohols to Aldehydes

Answer 17

Oxidise Primary Alcohol
Use Cr2O7- + H2SO4 Catalyst + Heat
RCH2OH + [O] → RCOH + H2O

Question 18

Alcohols to Carboxylic Acids

Answer 18

Oxidise Primary Alcohol
Use Cr2O7- + H2SO4 Catalyst + Heat under Reflux
RCH2OH + [O] → RCOOH + H2O

Question 19

Alcohols to Ketones

Answer 19

Oxidise Secondary Alcohols
Use Cr2O7- + H2SO4 Catalyst
RCH(OH) + [O] → RCOR + H2O

Question 20

Alcohols to Chloroalkanes

Answer 20

No H2O + Pure Alcohol
C2H5OH + PCl5 → C2H5Cl + POCl3 + HCl

Question 21

Alcohols to Bromoalkanes

Answer 21

Use 50% concentrated H2SO4 + Warm Temperature
C2H5OH + Br- → C2H5Br + OH-

Question 22

Alcohols to Iodoalkanes

Answer 22

Use Red Phosphorus + Heat under Reflux
2P + 3I2 → 2PI3
3C2H5OH + PI3 → 3C2H5I

Question 23

Alcohols to Alkenes

Answer 23

Use Heat + Concentrated H2SO4
C2H5OH → C2H4 + H2O

Question 24

Acyl Chlorides to Esters

Answer 24

Addition-Elimination Reaction
RCOCl + ROH → RCOOR + HCl

Question 25

Acyl Chlorides to Carboxylic Acids

Answer 25

Addition-Elimination Reaction RCOCl + H2O → RCOOH + HCl

Question 26

Acyl Chlorides to Amides

Answer 26

Addition-Elimination Reaction RCOCl + NH3 → RCONH2 + (NH4)+Cl-

Question 27

Acyl Chlorides to Secondary Amides

Answer 27

RCOCl + RNH2 → RCONHR + (RNH2)+Cl-

Question 28

Preparation of Grignard Reagant

Answer 28

Use Dry Ether RBr + Mg → RMgBr

Question 29

Grignard Reagant to Primary Alcohols

Answer 29

Use Strong Acid + Alcohol CH3OH + CH3MgBr → CH3CH2OH

Question 30

Grignard Reagant to Secondary Alcohols

Answer 30

Use Strong Acid + Aldehyde CH3COH + CH3MgBr → CH3CH(OH)CH3

Question 31

Grignard Reagant to Tertiary Alcohols

Answer 31

Use Strong Acid + Ketone CH3COCH3 + CH3MgBr → CH3C(OH)(CH3)CH3

Question 32

Grignard Reagant to Carboxylic Acids

Answer 32

Use Strong Acid + CO2 CO2 + CH3MgBr → CH3COOH

Question 33

Aliphatic Reduction of Nitriles to Amines

Answer 33

Use LiAlH4 + Dry Ether RCN + [H] → RCH2NH2

Question 34

Aromatic Reduction of Nitriles to Phenylamine

Answer 34

Use HCl + Tin Catalyst C6H5NO2 + [H] → C6H5NH2

Question 35

Reduction of Carboxylic Acids

Answer 35

Use LiAlH4 + Dry Ether RCOOH + [H] → RCH2OH

Question 36

Carboxylic Acids to Acyl Chlorides

Answer 36

RCOOH + PCl5 → RCOCl + POCl3 + HCl

Question 37

Carboxylic Acids to Esters

Answer 37

Heat under Reflux + Use concentrated H2SO4 RCOOH + ROH → RCOOR + H2O

Question 38

Halogenoalkanes to Amines

Answer 38

Use Heat + Ethanolic NH3 + NO H2O C2H5Br + NH3 → C2H5NH2

Question 39

Halogenoalkanes to Alcohols

Answer 39

Use NaOH + Heat under reflux + In aqueous conditions C2H5Br + OH- → C2H5OH

Question 40

Halogenoalkanes to Nitriles

Answer 40

Use Ethanolic KCN + Heat under Reflux + NO H2O C2H5Br + CN- → C2H5CN

Question 41

Halogenoalkanes to Alkenes

Answer 41

Use Ethanolic KOH + Heat under Reflux C2H5Br + OH- → C2H4