Question

(e) (15 pts) When compound I undergoes the chemical transformations seen below, two new carbonyl compounds are formed (III and IV). 1 equivalent of MgBr I DIBAL-H III (major organic product) IV (major organic product) 1) (6 pts) Provide the structures for compounds III and IV. (11) (9 pts) Which of the two carbonyl compounds is more susceptible to nucleophilic addition: III or IV ? Provide two reasons for your choice. (1) pts) Rank the following compounds in the order of increasing the percentage of hydrate at equilibrium. - Hye ji V VI VII VIII M IV - the major the major organic product organic product from (e) - from (e) -

Answer 1

DIBAL-H 1 eq MgBr IV will be more reactive because it as an aldehyde and the CEO is more reactive in comparison to Ill which is a ketone. Aldehyde is more reactive because it is sterically les hindered as there is no methyl on the other side. Secondly Ketone is less reactive becasue it has a methyl group instead of H which donates electron density to C=0 through inductive effect. order of reactivity: masih syysty