Organic Chemistry 1 - Reagents and Conditions

Question 1

Hydration of alkenes

Answer 1

Steam with conc H3PO4 catalyst at 300°C

Question 2

Hydrogenation of alkenes

Answer 2

H2 with Ni catalyst

Question 3

Electrophilic addition of an alkene to form a mono-substituted bromoalkane

Answer 3

HBr

Question 4

Electrophilic addition of an alkene to form a di-substituted bromoalkane

Answer 4

Br2

Question 5

Free radical substitution of alkanes

Answer 5

Cl2(g) and UV light

Question 6

Nucleophilic substitution of haloalkane to form alcohol

Answer 6

OH-(aq) heat under reflux

Question 7

Nucleophilic substitution of haloalkane to form amine

Answer 7

Excess ethanolic NH3, heated in a sealed tube

Question 8

Nucleophilic substitution of haloalkane to form nitrile

Answer 8

KCN in ethanol, heat under reflux

Question 9

Partial oxidation of primary alcohol

Answer 9

K2Cr2O7 / H+, heat and distil

Question 10

Full oxidation of primary alcohol

Answer 10

K2Cr2O7 / H+, heat under reflux

Question 11

Oxidation of tertiary alcohols

Answer 11

No reaction

Question 12

Dehydration of alcohols

Answer 12

Al2O3 at 300°C or conc H2SO4 cat at 170°C or heated with conc H3PO4 cat

Question 13

Substitution of the OH group in alcohols for chlorine

Answer 13

PCl3, PCl5 or SOCl2

Question 14

Substitution of the OH group in alcohols for bromine

Answer 14

Warm conc H2SO4 and NaBr or red phosphorus and Br2

Question 15

Substitution of the OH group in alcohols for iodine

Answer 15

Warm conc H3PO4 and NaI or red phosphorus and I2

Question 16

Reagent that will react with both alcohols and carboxylic acids to produce sodium alkoxides and carboxylates

Answer 16

Na

Question 17

Iodoform reaction

Answer 17

I2(aq) / OH-

Question 18

Esterification of alcohols

Answer 18

Carboxylic acid and conc H2SO4 catalyst

Question 19

Oxidative cleavage of alkenes

Answer 19

Hot, acidified, conc KMnO4

Question 20

Oxidative addition of alkenes

Answer 20

Cold, acidified, dilute KMnO4

Question 21

Reagent that will reduce carbonyls and carboxylic acids

Answer 21

LiAlH4 in dry ether

Question 22

Reagent that will only reduce carbonyls and not carboxylic acids

Answer 22

NaBH4 in alkaline aqueous methanol

Question 23

H2(g) with Ni or Pt catalyst

Answer 23

Catalytic hydrogenation of carbonyls

Question 24

Nucleophilic addition of carbonyls to form cyanohydrins

Answer 24

HCN with NaCN catalyst

Question 25

Condensation of carbonyls

Answer 25

2,4-DNPH

Question 26

Elimination of haloalkanes

Answer 26

Ethanolic OH- heat under reflux

Question 27

Reagent that will react with only carboxylic acids to produce sodium carboxylates

Answer 27

NaOH or NaHCO3 or Na2CO3

Question 28

Hydrolysis of nitriles to form carboxylic acids

Answer 28

H2SO4 (aq) and heat under reflux

Question 29

Hydrolysis of nitriles to form sodium carboxylates

Answer 29

NaOH (aq) and heat under reflux

Question 30

Heat under reflux with H2SO4(aq)

Answer 30

Hydrolysis of esters to produce carboxylic acids

Question 31

Heat under reflux with NaOH(aq)

Answer 31

Hydrolysis of esters to produce sodium carboxylates

Question 32

Fehling's reagent (alkaline solution of Cu2+)

Answer 32

Oxidation of aldehydes to form carboxylate ion, which gives a characteristic brick red ppt

Question 33

Tollens' reagent (alkaline solution of Ag+)

Answer 33

Oxidation of aldehydes to form carboxylate ion, which gives a characteristic silver mirror