SLE214 tutorial 5 SOLUTIONS

Q1. Use your knowledge of resonance structures and aromaticity to predict why the protonated form of 4-pyrone (shown) is so stable.
H O H O H O Either the second or th ird res str ucture (there are more that i havent shown) can be evaluated to ascertain whethe r it is ar omatic a nd the answe r = yes There fore the comp ound is more stable than you might think.

Q2. Predict the first product formed from the following reactions.

O O CH3 CH2COCl AlCl 3 O The two groups - alkyl and ethermake the left hand ring more reactive. Of these the O is the most activating therefore substitution (o,p) is observed

Q3. Using retrosynthetic analysis, devise a forward synthesis of the following:

Br

add SO3 H Br SO3H

FGI

Br

Bromination

F-C acylation

Above is the retrosynthetic analysis: Actual synthesis is reverse of this - need to get reagents exactly right for each transformation. This has been in the past a test question. Q4. Use your knowledge of alkene reactions and resonance to predict which of these two substrates will react faster with HBr. Its all to do with the ccat intermediate.
H Br v. stab le (al l atoms have o ctet)

Nicely sta bilised carb ocation = low en ergy intermedia te which means r apid reactio n pr ogress S ame anal ysis on nitro compou nd shows an unsta ble i nter med iate therefor e slow pr ogress H Br no t stable

O2 N

O 2N

O2N

O2 N