Question

#1. Using curved arrows to symbolize electrons, write a complete reaction mechanism for the bromination of acetanilide to create the product. Include the resonance structures for any charged, delocalized intermediates that are involved.

#2. Why does performing the experiment at 0 degrees Celsius help you identify some of the relative rates of reactivity?

#3. Explain why a methyl group is a mildly activating group while a methoxy group is strong activating.

#4. Explain why-- NH2 act as an activator and-- NO2 act as a deactivator. Include resonance and charges in your explanation.

#5. Draw ALL of the intermediate resonance structures that would occur if bromine were added to anisole. Draw the possibilites for ortho-addition, meta-addition, and para-addition and explain why some addition sites will be preferred using your resonance structures.

Answer 1

Part 1) HN HN Br2 AlBr3 (Major Product) Mechanism AlBr3 Br -Br Br +AlBr4 HN HN HN HN Br Br Br Br HN Part 2) The rate of electrophilic substitution reaction can be slowed down by decreasing the reaction temperature and help in determining the relative rate

Part 3) CH3 : OCH3 Methoxy group is strongly activating than menthy group, because the two lone pair of electrons can be donated to the ring and can activate the ring, whereas there is no lone pair of electrons on methyl group Part 4) NH2 group increase the electron density on the ring by donating lone pair of electrons of Nitrogen. This activates the ring NH2 NH2 : NH NH2 NO2 group decrease the electron density on the ring and activates the ring но но но

Part5) Methoxy group of anisole is ortho, para directing (Activator), therefore, meta substitution is not possible Mechanism AlBr3 Br_Br Br+ : O O: Br Br : O : O Ortho product Para product