Organic Chemistry

Problem # 727

Show how the ester below can be prepared from propene.

Problem # 726

Show two esters that would yield the two alcohols below after treatment with lithium aluminum hydride.

Problem # 725

A chemist carried out a Fischer esterification using methanol that was isotopically labeled with 18O (indicated with an asterisk).

Which one of the esters below (A-D) was formed?

Problem # 724

Use curved arrows to show the formation of the tetrahedral intermediate of a Fischer esterification reaction (shown below). There are three steps in total.

Problem # 723

Show how to prepare each compound from vinyl benzene.

How would you prepare the methyl ester of each compound?

Problem # 722

Show how to prepare vinyl benzene from benzene.

Problem # 721

Rank each of the four compounds below in order of decreasing acidity (1 = most acidic).

Problem # 720

Base your answers to the three problems below on your knowledge of electron donating groups and electron withdrawing groups (EDG and EWG).


a) Based on the pKa's listed below, Is formic acid more or less acidic than acetic acid? Propose an explanation why.

b) If acetic acid were added to a pH = 4.7 buffer solution, what percentage of it would be in its acetate (conjugate base) form?

c) Methoxy (-OCH3) is usually considered an EDG. But based on the pKa of methoxy acetic acid, do you think this is always the case? Explain.

Problem # 717

Rank each of the eight compounds A through H below in order of decreasing acidity (1 = most acidic).


Don't get intimidated! What are the differences between these compounds?

Consider electron withdrawing groups (EWG), resonance, hybridization, and the functional group of the acidic proton.

Problem # 715

α-D-glucose is shown below.

a) Is α-D-glucose an acetal, hemiacetal, ketal, or hemiketal?

b) Draw the carbonyl form of α-D-glucose.