These are the homework exercises to accompany the Textmap for McMurry's Organic Chemistry textbook.
Name the following compounds using IUPAC conventions
- 3-methylpentanoyl chloride
- propyl 2-methylpropanoate
- tert-butyl cyclopentanecarboxylate
- 1-methylbutylcyclopentane carboxylate
- (S)-2-hydroxypropanoyl phosphate
- propyl 2,3-dimethyl-2-butenethioate
How would you create the following esters from the corresponding acids?
The following molecule is treated with acid and undergoes an intramolecular Fischer Esterification. Draw the product.
- Acetic acid + ethanol
- Butanoic acid + isopropanol
- Cyclohexanecarboxylic acid + propanol
Draw the mechanism for the following reaction
Propose a synthesis of the following molecules from an acid chloride and an amide.
- Acetyl chloride and dimethylamine
- Benzoyl chloride and ethylamine
- Acetyl chloride and ammonia
Draw out the mechanism for the following reaction.
Draw the product of the reaction between these two molecules.
Why is the alkaline hydrolysis of an ester not a reversible process? Why doesn't the reaction with a hydroxide ion and a carboxylic acid produce an ester?
Draw the product of the reaction between the following molecule and LiAlH4, and the product of the reaction between the following molecule and DIBAL.
How might you Prepare the following molecules from esters and Grignards?
The reaction between a carboxylic acid and a hydroxide ion is an acid base reaction, which produces water and a carboxylate anion.
How would you prepare the following compounds from N-Propypl benzamide?
Propose a synthesis for the following.
- NaOH, H2O
- NaOH, H2O, then LAH