Carboxylic Acids & Nitriles

Rank the following substituents on a carboxylic acid to make the acid most acidic to least acidic: H, CH₃, CH₂Cl

CH₂Cl, H, C_H3

In what conditions will a carboxylic acid be in its carboxylate form (deprotonated)?

pH>pKa

In what conditions will a carboxylic acid be in its protonated form?

pH<pKa

What kind of reaction do carboxylic acid derivatives undergo?

Substitution

Rank the following leaving groups as best to worst: ester, anhydride, acid chloride, amide

acid chloride, anhydride, ester, amide

What can you use to preform acyl chloride synthesis from carboxylic acids?

SOCl₂ & Pyridine

What is Fischer Esterification?

Making esters from carboxylic acids using an alcohol with acid catalyzed conditions

What is the acronym for the steps of Fisher Esterification?

PADPED

What are lactones and how are they made?

Cyclic esters made from a molecule with a carboxylic acid group on one end and an alcohol on the other end

What do you make when you have a molecule with both an aldehyde and an alcohol?

Hemiacetal (cyclic)

What do you use to turn an aldehyde/ketone into a cyanohydrin?

NaCN & HCN

What conditions can a nitrile hydrolysis reaction take place?

Acidic & Basic

What is they key intermediate when preforming hydrolysis on a nitrile in basic conditions?

Amide

What do you make when you treat a nitrile with a grinyard reagent?

Ketone via Imine intermediate 

What do you use to form an amine from a nitrile?

LiAlH₄ with ether followed by acid workup