Organic Chemistry Chapters 19–20: Carbonyl Reaction Mechanisms

When do you use NaP in Chapter 19?

Aldehydes/ketones + strong nucleophiles: Grignard, hydride, or cyanide

What does NaP stand for?

Nucleophilic attack → Protonation

Aldehyde/ketone + Grignard (RMgX), then H₃O⁺

Attack → Protonation; C-C bond forms and an alcohol results

Aldehyde/ketone + hydride (NaBH₄ or LiAlH₄), then workup

Hydride attack → Protonation; carbonyl becomes alcohol

Aldehyde/ketone + CN⁻/HCN

CN⁻ attack → Protonation; cyanohydrin forms

When do you use NyPD PLeaD in Chapter 19?

Aldehydes/ketones + ammonia or primary/secondary amines

Aldehyde/ketone + NH₃ or primary amine

Forms an imine

Aldehyde/ketone + secondary amine

Forms an enamine

When do you use PaNDa in Chapter 19?

Aldehydes/ketones + weak nucleophiles under acid catalysis, especially alcohols

What does PaNDa stand for?

Protonation → Nucleophilic attack → Deprotonation

Aldehyde/ketone + alcohol under acid; first addition

Protonate carbonyl → Alcohol attacks → Deprotonate; hemiacetal forms

When do you use PLaNDa in Chapter 19?

Acid-catalyzed conversion of a hemiacetal to an acetal using alcohol

What does PLaNDa stand for?

Protonate → Leaving group leaves → Nucleophile attacks → Deprotonate

Hemiacetal + alcohol under acid

Protonate OH → H₂O leaves → Alcohol attacks → Deprotonate; acetal forms

When do you use NaL NaP in Chapter 20?

Acid chlorides, acid anhydrides, or esters + strong nucleophiles: Grignard or hydride

When do you use NaL in Chapter 20?

Acid chlorides, acid anhydrides, or esters + moderately strong nucleophiles: Gilman, bulky hydride, acetate, or cyanide

When do you use NaLD in Chapter 20?

Acid chlorides/anhydrides + water, alcohols, or amines; also hydroxide hydrolysis under basic conditions

When do you use PaNDa PLaD in Chapter 20?

Esters/acids + weak nucleophiles under acid catalysis, especially esterification and hydrolysis

Acid chloride + water

Carboxylic acid

Acid chloride + alcohol

Ester

Acid chloride + amine

Amide

Acid chloride or anhydride + hydroxide under basic conditions

Carboxylate

Carboxylic acid + alcohol under acid

Ester + water

Ester + water under acid

Carboxylic acid + alcohol

What is the key difference between NaP and NaL NaP?

NaP: carbonyl addition; NaL NaP: acid-derivative reactions can involve addition then leaving-group loss

What is the key difference between NaLD and PaNDa PLaD?

NaLD covers neutral protic nucleophiles/basic hydroxide; PaNDa PLaD covers weak nucleophiles under acid catalysis