Which of the following will undergo Friedel-Crafts alkylation with (CH3)3CCl, AlCl3 most rapdily?
A. acetophenone
B. toluene
C. cyanobenzene
D. benzenesulfonic acid
E. iodobenzene
2007-05-16 10:37:25 · 3 answers · asked by jeanettervetr 2 in Science & Mathematics ➔ Chemistry
Toluene is activated towards electrophilic substitution.
2007-05-16 10:42:38 · answer #1 · answered by Gervald F 7 · 1⤊ 0⤋
An electrophile means "electron-loving". By electrostatics you expect that an electrophile is positively charged or at least has positive property to it. Eleminate C because it is full of electron cloud. A. is the right answer because in alkylation, you are adding an alkyl group. A carbocation or carbonium is an electrophile. The alkyl halide is a good source of alkyl cation or carbocation, once the Chloride is separated. Note that Cl-1 is a stable anion and it is just happy to be separated from another ensuing stabel carbocation. OOps. I did not see you wanted an ORTHO alkylation. That is in the ortho position. Note that this is a congested postion to add a large alkylcation. Thus, the best answer is B. the H+, because it prevents or will not encounter steric hindrance effects.
2016-05-20 02:22:39 · answer #2 · answered by charlotte 4 · 0⤊ 0⤋
Which aromatic bears the most activating (electron donating, by sigma-polarization or pi-resonance) group?
2007-05-16 10:42:16 · answer #3 · answered by Uncle Al 5 · 0⤊ 0⤋