Question

all three questions

Application Questions 1. Draw the mechanism for the sulfonation of benzene. Use HSO as the electrophile. Draw the all the resonance structures of the stabilized cation intermediate 2. Draw the major product formed when each of the following compounds is treated with Cly/AICI, Assume chlorination only occurs in one position on the ring rather than multiple positions. COM COCX ooo 3. Predict whether toluene or chlorobenzene would undergo electrophilic aromatic substitution more quickly when treated with C1z/AICI. Explain your prediction. Draw the major product for each of the two reactions

Answer 1

1) sulfonation of benzene involves following steps- Step-I 303 + H₂SO - HSO + HSO Step-I PAH + HSO 2 FT " + Hy soy

Then follows the following 0 = The ehtorination mechanism steps first R- step-I 80 m Alel + ale d- Alely oze Now He ezo He -e o Herero Herero Again So electrophilie aromatic chlorination cannot take place on ortho and para position because of positive charge presence so meta will be mayor product (0) el-Alely evenz coch 3 el - Alely again o Coch 5=é-en ortho & barca due to abundance so mayor products are of electrons Again Deoca, o-corta el - Alely Decent as par

-0Hz öeoen, õ - e-oet o- e-oeH3 80 meta will be major product o=e-OCH O =C-Oen 3 Again port, 11 - ve Here _ex, group will block parca position anak but as meta product is dominant and due to ti & effect on the ring chlorination will seewee more readily compared to (A) coet I- Alely 4 Lel ocort. El = Here para position is blocked so or tho. will be major product more re реоена to 6) I el-Alely MA Again ht Ft TE as para position is blocked ma pe s produet will be ortho el-Aiely

D Here ehl ere ehloro benzene will undergo chlorination more readily compared to toluene because -d group as has strong +R effect on the benzene ring. Although est group of toluene has +I effect on the benzene ring but this far more effective compared to + I effect. ett3 (Toluene) .Cehlorobenzenet el-Alely