Organic Pathways - Aliphatic

Question 1

Alkene to alcohol

Answer 1

H3PO4
High temp and pressure
Electrophilic addition

Question 2

Alcohol to alkene

Answer 2

Conc H2SO4
180°
Dehydration/Elimination

Question 3

Alcohol to aldehyde/ketone

Answer 3

Acidified potassium dichromate
H2SO4
Heat

Question 4

aldehyde/ketone to alcohol

Answer 4

NaBH4 in water with methanol
Reduction

Question 5

Haloalkane to alcohol

Answer 5

KOH aqueous
Heat under reflux
NucSub

Question 6

Nitrile to 1° amine

Answer 6

H2, Ni 200°C or LiAlH4 in ether
Reduction

Question 7

1° amine to 2° amine

Answer 7

Acyl chloride
Room temp

Question 8

Haloalkane to 1° amine

Answer 8

Ethanolic NH3
Heat under pressure
NucSub

Question 9

Alkane to haloalkane

Answer 9

Halogen eg Cl2 Br2
UV light
(Free rad)

Question 10

Haloalkane to Alkene

Answer 10

Ethanolic KOH
Hot reflux

Question 11

Haloalkane to nitrile

Answer 11

Ethanolic KCN
Heat, Reflux

Question 12

Alkene to haloalkane

Answer 12

HX
Eg HBr, HCl

Question 13

Carboxylic acid to ester

Answer 13

Alcohol + conc H2SO4
(Esterification)

Question 14

Ester to carboxylic acid

Answer 14

Dilute H2SO4, H20 or dilute NaOH
Reflux

Question 15

Alcohol to ester

Answer 15

Carboxylic acid + conc H2SO4
Heat
Esterification

Question 16

Aldehyde/Ketone to hydroxynitrile

Answer 16

HCN + H2SO4

Question 17

Aldehyde/ketone to carboxylic acid

Answer 17

Acidified potassium dichromate, H2SO4 + heat
Or
Tollens/fehlings

Question 18

Alkene to alkane

Answer 18

H2
Nickel catalyst
200C°

Question 19

Alkene to Alkyl Hydrogensulfate

Answer 19

Conc H2SO4

Question 20

Alkyl Hydrogensulfate to alcohol

Answer 20

Dilute and warm

Question 21

Amine to amide

Answer 21

Acyl chloride/acid anhydride

Question 22

In aromatics what is the mechanism

Answer 22

ELECTROPHILIC substitution/addition (alkenes)

Question 23

What are the two mechanisms from electrophilic substitution

Answer 23

• nitration (if Nitrate group)
• friedel crafts acylation