ochem2 week 10 part 1

What are nitriles?

Nitriles are organic compounds containing a cyano ($-C\equiv N$) group.

How do you name a nitrile when the nitrile carbon is at position 1?

Name the compound using standard IUPAC rules and add "nitrile" (e.g., 4-methylpentane nitrile).

How do you name a nitrile when the nitrile carbon is not at position 1?

Treat the cyano group as a substituent and name it as "cyano" (e.g., 4-cyanobutanoate).

How are esters named?

Esters are named using the suffix "oate".

How are thioesters named?

Thioesters are named by replacing "oate" with "thioate".

How are acyl phosphates named?

Acyl phosphates are named after the attached groups followed by "phosphate".

What are the key steps in a Grignard reaction with esters?

The Grignard reagent attacks the carbonyl carbon of the ester, the pi bond breaks, a leaving group departs, and the negative charge is stabilized internally leading to product formation.

What are the steps in a nucleophilic acyl substitution mechanism?

1. Attack the carbonyl carbon by the nucleophile. 2. Formation of a tetrahedral intermediate. 3. Departure of the leaving group. 4. Regeneration of the carbonyl group and protonation, leading to the final product.

List the reactivity of acid derivatives from most to least reactive.

Acid Chlorides (most reactive) > Anhydrides > Esters > Thioesters > Amides (least reactive).

What principle explains the reactivity differences among acid derivatives?

More unstable leaving groups yield faster reactions due to more favorable bond dissociation energy.

What is the preferred method for synthesizing anhydrides?

Reacting acid chlorides with carboxylic acids at lower temperatures using a base catalyst (e.g., pyridine, triethylamine).

What are the common reactants and catalyst for Fischer Esterification?

A combination of carboxylic acid and alcohol, requiring a strong acid catalyst (commonly sulfuric acid).