5 In the Fischer esterification reaction, a carboxylic acid reacts with an excess of alcohol in acidic conditions to form an ester. During the reaction the sp2 hybridized carbonyl carbon of the acid forms an sp3 hybridized intermediate before returning to sp² hybridization in the product. Draw the structure of the neutral sp³ hybridized intermediate and the ester product in the reaction between pentanoic acid and n-propanol. pentanoic acid + n-propanol Draw the neutral sp³ intermediate. Select Draw Templates More ////// C H O H+ propanol neutral sp³ intermediate Erase Draw the ester product. ester product Select Draw Templates More C H O Erase

Salsalate, which is an ester formed by the reaction of two molecules of salicylic acid, is another salicylate used as an aspirin alternative for those who are hypersensitive to aspirin. Draw the structures of salicylic acid and salsalate.

Name the sodium salt of the carboxylic acid that is formed by the saponification (basic hydrolysis) of the following ester with sodium hydroxide:

Alkenes can be converted to alcohols by reaction with mercuric acetate to form a β-hydroxyalkylmercury(II) acetate compound, a reaction called oxymercuration. Subsequent reduction with NaBH4 reduces the C–Hg bond to a C–H bond, forming the alkyl alcohol, a reaction called demercuration. Draw the structures of the Hg-containing compound(s) and the final alcohol product(s) formed in the following reaction sequence, omitting byproducts. If applicable, draw hydrogen at a chirality center and indicate stereochemistry via wedge-and-dash bonds.