An NO2 group sits on a benzene ring. Where does the next group land?

• At the ortho or para spots
• At every spot with equal ease
• At the meta spot

An OH group sits on a benzene ring. Where does the next group land?

• At the ortho or para spots
• At the meta spot only
• At every spot with equal ease

A chlorine atom on a benzene ring speeds the ring up and directs newcomers to the meta spot.

For phenol, why is ortho attack favoured over meta attack?

• Ortho attack avoids the intermediate entirely
• One resonance form puts the positive charge next to the oxygen lone pair, which steadies it
• Meta attack gives more resonance forms than ortho attack

Why does a halogen direct ortho and para even though it slows the ring?

• Its lone pairs steady the intermediate by resonance
• It donates protons to the ring on those routes instead
• It blocks the meta spot with its large size

You need bromine meta to an amino group on benzene. Which order of steps works?

• Protect the amino group first, then brominate the ring fully
• Nitrate, brominate meta to the nitro group, then reduce
• Brominate first, then nitrate the ring

A student plans a Friedel Crafts alkylation on a ring carrying an NO2 group. What is wrong with the plan?

• Nothing is wrong, since every ring accepts Friedel Crafts steps
• The nitro group must be removed before any substitution can happen
• Friedel Crafts reactions fail on strongly deactivated rings such as this one

To make meta bromonitrobenzene from benzene, which order of steps works and why?

• Nitrate first, then brominate, since the nitro group steers the next group meta
• Brominate first, then nitrate, since bromine steers the next group meta
• Either order works, since the two groups never steer each other