Question

1. Fill in the missing reactants, reagents & conditions, or products. Indicate major product only, unless otherwise indicated with a +sign. Note that it is possible to have more than one correct answerl SO3H -O Cl AlCl3 HNO3 H2SO4 он он SO3H Me

Answer 1

1)

a) AlCl₃ is a strong Lewis acid and will acquire the Cl from the solution mixture. This will make the remaining electron deficient part of the molecule to attach the electron-rich sulfonated benzene ring. The presence of Oxygen groups in the sulfate molecule results into -I effect and thus decreases the electron density of the ring making the ring a Meta directing entity. Hence the incoming electrophile will attack at the Meta position.

b) Nitration of phenol. As phenol is electron donating group, it is an ortho-para directing entity and the electrophile (i.e NO₂⁺ ) will attack those specific positions only. The para substituted product will be the major product due to the extra stability. In case of ortho-substituted product due to electronic repulsions of the neighboring groups, the molecule is bit unstable.

c) As the para position is already taken up by the Methyl group the sulfate will have to attach on ortho position itself. No other position is possible.