Reactions

Question 1

Alkane to RX

Answer 1

FRS: Cl2(g) or Br2(g) uv light

Question 2

Alkene to Alkane

Answer 2

Reduction: H2(g), Ni, 200C

Question 3

Alkene to HX

Answer 3

EA: HX(g), rt

Question 4

Alkene to HX (inert solvent)

Answer 4

EA: Cl2/Br2 in CCl4, rt, dark

Question 5

Alkene to HX (H2O)

Answer 5

EA: Cl2/Br2, rt

Question 6

Alkene to Alcohol

Answer 6

EA: 1) conc H2SO4 cold, warm w water

2) steam, H3PO4 cat, 300C, 60atm

Question 7

Alkene to 2OH

Answer 7

Oxidation: 1) KMnO4, in NaOH (aq), cold

2) KMnO4 in dilute H2SO4, cold

Question 8

Arene to NO2

Answer 8

NItration: conc HNO3, conc H2SO4, <55C (30C for ethylbenzene)

Question 9

Arene to X

Answer 9

Halogenation: X2, AlX3/FeX3, rt

Question 10

Arene to R

Answer 10

FCA: RX, AlX3/FeX3, rt

Question 11

Arene to Alkane

Answer 11

Catalytic Hydrogenation: H2, Ni cat, 200C, 30atm

Question 12

Arene to methylbenzene

Answer 12

FCA: CH3Cl, excess benz, anhydrous AlCl3 cat, 40C

Question 13

Methylbenzene to benzoic acid

Answer 13

SCO: KMnO4 in dil H2SO4, hur, forms white ppt upon cooling

Question 14

HX to Alcohol

Answer 14

NS/alk hydrolysis: NaOH/KOH (aq), hur

Question 15

HX to Nitrile

Answer 15

NS: ethanolic NaCN/KCN, hur

Question 16

HX to Amine

Answer 16

NS: xs ethanolic NH3, hst

Question 17

HX to Alkene

Answer 17

Elim: ethanolic NaOH/KOH, hur

Question 18

OH to Alkene

Answer 18

Elim:

1) XS conc H2SO4, 170C
2) Al2O3, cat, 350C
3) conc H3PO4, cat, 200-250C

Question 19

OH to RX + H2O

Answer 19

NS:

1) conc HCl, ZnCl2 cat, heat
2) HBr/I rt

Question 20

OH to RX + H3PO3 (L)

Answer 20

NS:

1) anhydrous PX3, heat

Question 21

OH to RX + POCl3 + HCl

Answer 21

NS: anhydrous RCl5

Question 22

OH to RX + SO2 + HCl

Answer 22

NS: anhydrous SOCl2 heat

Question 23

1° OH to ald

Answer 23

Oxi: K2Cr2O7, H2SO4, hid

Question 24

1° OH to COOH

Answer 24

Oxi: K2Cr2O7, H2SO4, hur

KMnO4, H2SO4, hur

Question 25

2° OH to ket

Answer 25

Oxi: K2Cr2O7, H2SO4, hur | KMnO4, H2SO4, hur

Question 26

Triiodomethane/Iodoform

Answer 26

Oxi: RCH(OH)(CH3) + 6NaOH + 4I2 --> RCOO-Na+ + CHI3 + 5NaI + 5H2O

Question 27

COOH + OH to ester

Answer 27

NS: conc H2SO4, cat, heat, double arrow

Question 28

COCl + OH to ester + HCl

Answer 28

NS: r.t.

Question 29

COOH + phenol

Answer 29

no rxn

Question 30

COCl + phenol to ester + HCl

Answer 30

NS: r.t.

Question 31

phenol to trisub

Answer 31

ES: 1) Br2(aq), rt (white ppt) | 2) conc HNO3, rt

Question 32

phenol to 1sub

Answer 32

ES: 1) Br2 in CCl4, rt | 2) dilute HNO3, rt

Question 33

CHO to COOH (ket no rxn)

Answer 33

Oxi: K2Cr2O7, H2SO4, hur | KMnO4, H2SO4, hur

Question 34

CHO to 1°OH

Answer 34

Red: 1) LiAlH4 in dry ether, rt 2) NaBH4, methanol, rt 3) H2, Ni cat, heat 4) H2, Pd/Pt cat, rt

Question 35

ket to 2°OH

Answer 35

Red: 1) LiAlH4 in dry ether, rt 2) NaBH4, methanol, rt 3) H2, Ni cat, heat 4) H2, Pd/Pt cat, rt

Question 36

ald/ket cyanodrins

Answer 36

NA: HCN, trace amt of NaCN, cold, 10-20C

Question 37

COOH to OH

Answer 37

Red: LiAlH4 in dry ether, rt

Question 38

COOH to COO-NH4+

Answer 38

AB: NH3 (aq), rt

Question 39

ester to OH

Answer 39

Red: LiAlH4 in dry ether, rt | 2 alcohols formed

Question 40

ester + H2O to COOH + OH

Answer 40

hydrolysis: HCl(aq), hur

Question 41

ester + OH- to COO- + OH

Answer 41

hydrolysis: NaOH(aq), hur

Question 42

CN to CH2NH2

Answer 42

Red: 1) LiAlH4 in dry ether, rt 2) H2, Ni cat, heat 3) H2, Pd/Pt cat, rt

Question 43

1° amide to 1°amine

Answer 43

Red: LiAlH4 in dry ether, hydrolysis w H2O

Question 44

NO2-benzene to NH2-benzene

Answer 44

Red: Sn in xs conc HCl, heat then [AB] NaOH(aq)

Question 45

RNH2 to RNH3+

Answer 45

AB: HCl/H2SO4

Question 46

RNH2 + RCOCl to amide + HCl

Answer 46

NS: anhydrous COCl, rt

Question 47

NH2-benzene + 3Br2

Answer 47

ES to form trisub + 3HBr

Question 48

amide + HCl + H2O to COOH and NH4+Cl-

Answer 48

Hydrolysis: HCl/H2SO4, strong heating

Question 49

amide + NaOH to COO-Na+ and NH2CH3

Answer 49

Hydrolysis: NaOH, strong heating

Question 50

amide to COOH and NH4+ salt

Answer 50

Hydrolysis: HCl/H2SO4, prolonged heating under reflux

Question 51

amide to COO- and RNH2

Answer 51

Hydrolysis: NaOH, prolonged heating under reflux