666 CHAPTER 16 Reactions of Substituted Benzenes
e. g. i. k.f. h. j. l.- Show how the following compounds could be synthesized from benzene:
a. N,N,N-trimethylanilinium iodide d. 2-methyl-4-nitrophenol g. p-dideuteriobenzene
b. benzyl methyl ether e. p-nitroaniline h. p-nitro-N-methylaniline
c. p-benzylchlorobenzene f. m-bromoiodobenzene- Which of the following compounds will react with HBr more rapidly?
- Give the product(s) obtained from the reaction of each of the following compounds with
a. c.b. d.- Which would react more rapidly with m-xylene or p-xylene? Explain.
- What products would be obtained from the reaction of the following compounds with
a. b. c.- A student had prepared three ethyl-substituted benzaldehydes, but had neglected to label them. The premed student at the next
bench said that they could be identified by brominating a sample of each and determining how many bromo-substituted products
were formed. Is the premed student’s advice sound? - Explain, using resonance contributors for the intermediate carbocation, why a phenyl group is an ortho–para director.
- Cl (^2) Cl
biphenyl
Cl
FeCl 3
CH 3
C(CH 3 ) 3
CH 2 CH 2 CH 2 CH 3
CHCH 3
CH 3
CH 2 CH 3
CH 3
Na 2 Cr 2 O 7 +H++¢?
Cl 2 +FeCl 3 ,
CH 3 O
NO 2
OC
O
H 3 C C COCH 3
OO
CH 2 O
Br 2 >FeBr 3 :
CH 3 CH CH 2 or CH 3 O CH CH 2
SO 3 H
OH
Cl
Cl
OCCH 3
O
CH 3 OC
O
OH CH 3 NO 2
CH 3
CH 3
NO 2
CCH 3
Br
O