Chapter 16

Question 1

Nitration

Answer 1

HNO3, H2SO4

Question 2

Sulfonation

Answer 2

SO3,H2SO4

Question 3

Halogenation

Answer 3

X2,FeX2(Cl or Br)

Question 4

Alkylation/Acylation

Answer 4

RCl, AlCl3 or RCOCl,AlCl3

Question 5

making NH2 a deactivator

Answer 5

CH3OCl, pyridine

to go back: -OH, H2O

Question 6

NO2 to NH2

Answer 6

1) Fe,HCl
  Zn(Hg), HCl
  H2,Ni
2)CF3COOH
  mild oxidizer or radical initiator

Question 7

SNAr (elim-addn)

Answer 7

strong ewg on ring ortho or para, nucleophile

Question 8

SNAr (elim-addn)

Answer 8

VERY strong base
Ex: KNH2, NH3 (l)
NaNH2, NH3 (l)
(product can be ortho, meta, or para)

Question 9

Other way to make benzyne

Answer 9

Mg, THF, heat

Question 10

Dow Process

Answer 10

1) NaOH, H2O, 340 C, 170 atm

2) H3O+

Question 11

Oxidation at benzylic position

Answer 11

a) KMnO4 or Na2Cr2O7, H2O, H2SO4, heat
b) NBS, CCl4, BzOH?
c) Br2, hv, CCl4

Question 12

reducing double bonds

Answer 12

H2, Pd, ethanol

Question 13

reducing benzylic ring

Answer 13

H2, Pt, 2000Psi, 25 C or

H2, Rh/C, ethanol, 1 atm

Question 14

how to reduce acyl group

Answer 14

1) H2, Pd/C, ethanol
2) Clemenson Reduction :Zn(H3), HCl, heat, diethylene glycol 3) Wolff-Kishner
step 1: NaCl, H2O, H2NNH2, diethylene glycol, heat step 2: H2O