Electrophilic Aromatic Substitution

Question 1

X2, FeX3

X= Cl or Br

Answer 1

halogenation, adds X to ring

Question 2

X2, FeX3
X= Cl or Br
mechanism

Answer 2

X2 and FeX3 combine to make X-X(+)-Fe(-)X3/Pi bond attacks an X/X-X bond breaks/makes FeX4 & leaves/forms cat near next to the X/FeX4 basic, deprot the H, elim/end: added X to ring, HX, FeX3

Question 3

HNO3, H2SO4

Answer 3

nitration, adds NO2

Question 4

HNO3, H2SO4

mechanism

Answer 4

HNO3 and H2SO4 combine to make nitro ion/Pi bond attacks N+ of nitro ion/one of O’s leave/adds just NO2 to ring/O(-)SO3H deprot the H, elim/end: added NO2 to ring, HOSO3H

Question 5

SO3, H2SO4

Answer 5

adds SO3H

Question 6

FC Alkylation;

reagents

Answer 6

benzene, RX, AlX3

Question 7

benzene, RX, AlX3

Answer 7

FC Alkylation; adds R to benzene

Question 8

benzene, RX, AlX3

mechanism

Answer 8

X from RX attacks Al of AlX3/R-X bond breaks, R forms cat, X-AlX3 forms/ Pi bond attacks R, forms cat on alpha position of where R attached/X of X-AlX3 deprot H on the same carbon as R, elim, double bond formed again.

Question 9

FC Acylation

Answer 9

adds acyl to benzene

Question 10

HNO3, H2SO4

nitronium mechanism

Answer 10

H(O)-N(+)=O-O(-) attacks (H)-OSO3H/H2O leaves/end:nitronium ion (N(+)O2)

Question 11

H2O, H2SO4

Answer 11

reverse sulfonation, benzenesulfonic acid –> benzene

Question 12

RX, AlX3

Answer 12

F.C. alkylation, changes H to R

Question 13

acyl halide, AlX3

Answer 13

adds acyl