carboxylic acids and carboxylic acid derivatives

Name two methods to form a carboxylic acid

1. Oxidation of a 1 prime alcohol with Jones reagent (CrO3 and H+, H2O)

2. Grignard reaction with CO2

List the carboxylic acid derivatives from most to least reactive - what is reactivity dependent on? what groups would react with just about anything with lone pairs of electrons?

1. Acid chloride

2. Acid anhydride

3. Carboxylic acid

4. Esters

5. Amides

Reactivity depends on how good of a leaving group it has (Cl- is a weak base and a great leaving group, NH2- is a very very strong base and a terrible horrible leaving group). Acid chloride and acid anhydride will react with lone pairs - big reactivity drop off at carboxylic acid, because -OH is a bad leaving group.

What is necessary in order for carboxylic acids, esters, and amides to react with a neutral nucleophile?

Catalytic hydrogen!!!

How to form an acid chloride from a carboxylic acid? What are the byproducts?

Use SOCl2 in a Sn2 reaction - product is acid chloride, byproducts are HCl and SO2.

How to form an acid anhydride - would this method work for an assymetric acid anhydride?

Two of the same carboxylic acids will perform a dehydration reaction under high temp and high pressure conditions - this only is useful to synthesize symmetric acid anhydrides.

when naming an ester, which group is the parent and which is the substituent? Which comes first in the name?

The carbon with 3 bonds to oxygen is part of the parent chain, and the group coming of of the oxygen is the substituent. Name the substituient first. (e.g., methyl ethanoate)

what is the suffix of an ester?

-oate

how would you form an ester from a carboxylic acid? Name necessary reagent and steps of mechanism?

Fischer esterification - use an alcohol group and catalytic hydrogen.

What is saponification - what are the final productions?

Saponification is the hydrolysis of an ester -it involves using a hydroxide ion to eliminate an alkoxide, which is a base and deprotonates the carboxylic acid. Final products are carboxylate and an alcohol.