Chem 214: Nucleophilic additions

What are the sections of this topic?

1. Hydrolysis reactions : 1.1 Esters, 1.2 Amides, 1.3 Nitriles

2. Aminolysis

3. Transesterification

4. Grignard reactions on esters

5. Weinreb Amide reaction

6. using acid chloride to make esters

7. making an acid chloride

What is a hydrolysis reaction?

It is the splitting of a molecule into its constituents using water (OH)

Show the mechanism for the base-catalysed hydrolysis of an ester with all solvents and reagents?

heated, solvent - Methanol or ethanol, strong base like NaOH for catalysis

Give the mechanism for hydrolysis of an amide with all necessary conditions, solvents, and reagents.

Strong acid (H2SO4 or HCl), water as a solvent, heating

Give the mechanism for the hydrolysis of a nitrile with all necessary solvents, reagents and conditions.

Reagents - strong acid like H3O+ and heat

What are the products of aminolysis?

An amide and an alcohol

Draw the mechanism for aminolysis with all the necessary reagents, conditions and solvents

room temperature, anhydrous solvents (DCM, THF)

What is transestirifcation?

A reaction where an ester reacts with an alcohol to form a new ester and new alcohol.

Draw the transesterification mechanism including all necessary reagents, solvents and conditions

temp - heated, base or acid catalyst

What is the reactivity series?

Acid chloride » Anhydride > aldehydes> ketones> esters » amines

Please draw the mechanism for an ester and Grignard reagent and describe the problem with this reaction?

The product of this reaction is a ketone, which is highly reactive and will continue to react with the Grignard reagent, resulting in an alkoxide. A ketone can be formed using Grignard reagent when reacting it with a Weinreb amide.

Draw the mechanism for the use of a Weinreb amide

What is the purpose of acid chlorides?

They are highly reactive acylating agents that introduce a RO- to other molecules, facilitating the formation of esters, ketones and amides.

Draw out the mechanism for the reaction of an acid chloride with a primary alcohol

Draw the mechanism for the production of an acid chloride and write down the needed reactants.

A carboxylic acid, and thional chloride.