Reaction Pathways

Question 1

arene sulfonation

Answer 1

c.H2SO4 (reflux)

Question 2

nitrating arene

Answer 2

c.HNO3, c.H2SO4 at <50C

Question 3

saturating arene

Answer 3

H2, Ni catalyst at 300C and 30atm

Question 4

arene alkylation

Answer 4

using haloalkane, AlCl3 catalyst (reflux)

Question 5

arene acylation

Answer 5

acylchloride, AlCl3 catalyst (reflux)

Question 6

arene chlorination

Answer 6

Cl2 (g), AlCl3 (makes Cl2 electrophilic enough to react with arene) catalyst at RT

Question 7

arene bromination

Answer 7

Br2 (l), FeBr3 (makes Br2 electrophilic enough to react with arene) catalyst at RT

Question 8

why is nitrating arenes done at low temperatures

Answer 8

protonated HNO3 very reactive - low temperatures to avoid multiple substitutions

Question 9

why is a catalyst used to chlorinate/ brominate/ nitrating arenes

Answer 9

makes them electrophilic enough to react with benzene

Question 10

what are the Friedel Crafts Reactions

Answer 10

alkylation and acylation

Question 11

what type of reactions are brominating/ nitrating/ sulfonating arenes

Answer 11

(electrophilic) aromatic substitutions

Question 12

alkene to dihaloalkane

Answer 12

Br2 (l)

Question 13

alkene to alkane

Answer 13

H2 (g), Pt catalyst

Question 14

alkene to alcohol

Answer 14

c. H2SO4, H2O (reflux)

Question 15

alkene to haloalcohol

Answer 15

Br2 (aq)

Question 16

alkene to haloalkane

Answer 16

HBr (aq), RT

Question 17

alkane to haloalkane

Answer 17

Cl2, UV light

Question 18

alcohol to alkene

Answer 18

Al2O3, 300C

Question 19

haloalkane to amine

Answer 19

c. NH3 (aq), heat in sealed tube

Question 20

haloalkane to alcohol

Answer 20

NaOH (reflux)

Question 21

alcohol to haloalkane

Answer 21

NaBr, c.H2SO4 (reflux)

Question 22

alcohol to ketone

Answer 22

acidified K2Cr2O7 (reflux)

Question 23

alcohol to aldehyde

Answer 23

acidified K2Cr2O7 (distil)

Question 24

alcohol to carboxylic acid

Answer 24

acidified K2Cr2O7 (reflux)

Question 25

aldehyde/ ketone to alcohol

Answer 25

NaBH4, H2O

Question 26

haloalkane to nitrile

Answer 26

CN-, ethanol (reflux)

Question 27

nitrile to amine

Answer 27

H2, Ni catalyst

Question 28

aldehyde/ ketone to hydroxynitrile

Answer 28

acidified NaCN (aq)

Question 29

aldehyde to carboxylic acid

Answer 29

acidified K2Cr2O7 (reflux)

Question 30

carboxylic acid to carboxylate

Answer 30

NaOH

Question 31

carboxylate to carboxylic acid

Answer 31

HCl (aq)

Question 32

carboxylic acid to ester

Answer 32

c. H2SO4 catalyst, alcohol

Question 33

ester/ amide to carboxylic acid

Answer 33

acid/ alkali (reflux)

Question 34

acid anhydride to ester

Answer 34

alcohol, RT

Question 35

acyl chloride to ester

Answer 35

alcohol, RT

Question 36

acyl chloride to primary amide

Answer 36

NH3, RT

Question 37

acyl chloride to secondary amide

Answer 37

NH2, RT

Question 38

ester hydrolysis with H2SO4, H2O

Answer 38

carboxylic acid + alcohol

Question 39

amide hydrolysis with H2SO4, H2O

Answer 39

carboxylic acid + amine salt

Question 40

ester hydrolysis with NaOH, H2O

Answer 40

carboxylate salt + alcohol

Question 41

amide hydrolysis with NaOH, H2O

Answer 41

carboxylate salt + amine

Question 42

how is carboxylic acid regained from carboxylate salt produced in basic hydrolysis of ester

Answer 42

adding acid (e.g. H2SO4) to re-protonate

Question 43

how is acyl chloride made from carboxylic acid produced in acidic hydrolysis of amide

Answer 43

adding SOCl2

Question 44

why is carboxylic acid produced in acidic hydrolysis of amide

Answer 44

catalyst is H2SO4 (no Cl2 to produce acyl chloride)