Organic Chemistry

Question 1

Alkene to alkane?
TOR?

Answer 1

H2(g), Ni catalyst, High P & T
Reduction

Question 2

Halogenoalkane to alkene?
TOR?

Answer 2

Alcoholic NaOH/KOH, heat
Elimination

Question 3

Alkene to alcohol?
TOR?

Answer 3

Steam, H3PO4 catalyst, high P & T
electrophilic addition

Question 4

Alkene to halogenoalkane?
TOR?

Answer 4

1) Dry HX(g) / HX in CCl4 -> hx
2) X2 (aq) -> x-oh
3) X2 in CCl4 in the dark / X2 (g or l) in the dark
Electrophilic addition

Question 5

Alkene to diol?
TOR?

Answer 5

Cold alkaline KMNO4
Mild oxidation

Question 6

What causes a cleavage in alkene?

Answer 6

Strong oxidation
Hot acidified KMNO4 or Hot alkaline KMNO4

Question 7

Alcohol to alkene?
TOR?

Answer 7

Excess conc H2SO4, heat
Elimination

Question 8

Halogenoalkane to nitrile?
TOR?

Answer 8

Ethanolic KCN, heat under reflux
Nucleophilic substitution

Question 9

Nitrile to amine?
TOR?

Answer 9

LiAlH4 in dry ether
Reduction

Question 10

Nitrile to carboxylic acid?
TOR?

Answer 10

HCl/H2SO4 (aq), heat under reflux
Acidic hydrolysis

Question 11

Alkane to halogenoalkane?
TOR?

Answer 11

Limited X2(g), UV light
FRS

Question 12

Alcohol to halogenoalkane?
TOR?

Answer 12

HX (g), heat, ZnCl2 anhydrous/ conc H2SO4
Anhydrous PCL3, PBr3, heat
Anhydrous PCL5 / SOCL2
Nucleophilic sub

Question 13

Primary alcohol to aldehyde?
TOR?

Answer 13

K2Cr2O7, H2SO4, heat with immediate distillation
Oxidation

Question 14

Aldehyde to carboxylic acid?
TOR?

Answer 14

K2Cr2O7/KMNO4, H2SO4, heat
Oxidation

Question 15

Secondary alcohol to ketone?
TOR?

Answer 15

KMNO4/K2CR2O7, H2SO4, heat
Oxidation

Question 16

Alcohol to ester?
TOR?

Answer 16

1) Acyl chloride; product: HCl
2) carboxylic acid, heat, H2SO4; product: H2O
Condensation

Question 17

Alcohol to alkoxide (RO-Na+)?
TOR?

Answer 17

Reactive metal (Na or K)
Redox/Acid-metal displacement

Question 18

What are carbonyl compounds?

Answer 18

Ketones and aldehydes

Question 19

Carbonyl compounds to cyanohydrin? (OH, CN Attached to C atom)
TOR?

Answer 19

HCN, trace amounts of NaOH as catalyst, cold
Nucleophilic addition

Question 20

Types of tests carbonyl compounds can undergo?

Answer 20

Oxidation - Tollen’s Reagent, Fehling’s Reagent
Condensation - 2,4-DNPH

Question 21

Carboxylic acid to acyl chloride?
TOR?

Answer 21

PCL5/ PCL3, heat/ anhydrous SOCL2
Nucleophilic acyl substitution

Question 22

Acyl chloride to carboxylic acid?
TOR?

Answer 22

H2O(l)
Nucleophilic acyl substitution/hydrolysis

Question 23

Carboxylic acid to alcohol?
TOR?

Answer 23

LiAlH4 in dry ether
Reduction

Question 24

Hydroxynitrile to hydroxycarboxylic acid?
TOR?

Answer 24

HCl (aq)/H2SO4(aq), heat under reflux
Acidic hydrolysis

Question 25

Halogenoalkane to amine? TOR?

Answer 25

Excess concentrated NH3 in ethanol, heat in sealed tube Nucleophilic substitution

Question 26

Acyl chloride to amide? TOR?

Answer 26

Primary amide: NH3 (g) Secondary amide: NH2R’ Tertiary amide: NHR’R’’ Condensation

Question 27

Amine to amide? TOR?

Answer 27

RCOCL Condensation

Question 28

Alkene to carboxylic acid? TOR?

Answer 28

Hot acidified/alkaline KMNO4, H2SO4/HCL(aq) Oxidation