Chapter 10--Aldehydes and Ketones: Nucleophilic Addition Reactions

Nature of Carbonyl Compounds

Naming Aldehydes

Aldehydes (-CHO) = drop “-e” from alkane and add “al” ending

• “carbaldehyde” ending if aldehyde is coming off of a cycloalkane

• Benzaldehyde if aromatic parent group

Naming Ketones

• Ketone = drop “-e” from alkane and add “-one” ending

• Both aldehydes and ketones are higher priority than alkanes, alkenes, halides, and alcohols.

• Aldehydes are a higher priority than ketones.

Name the following molecules using IUPAC naming.

• 3 chloro-2-methylhexanal

• 5-bromo-1-phenylpentan-2-one

What is the IUPAC name of the following structure?

4-methyl-5-phenylpentan-2-one

Which option below will result in the following molecule as the major organic product?

Reacting pentan-2-ol with sodium dichromate and acid

Nucleophilic Addition Reactions

Nucleophilic Addition Reactions

Nucleophilic Addition Reactions Summary

Nucleophilic addition: nucleophile adds to the carbon of the carbonyl group

Alcohol Formation: Reduction

Alcohol Formation: Grignard Reagents

Which option below will result in the following molecule as the major organic product?

Reacting pentan-2-one with sodium borohydride

AND

Reacting butanal with CH3MgBr, followed by treatment with acid

Hydrate Formation: Basic Conditions

Hydrate Formation: Acidic Conditions

Acetal Formation Mechanism

Acetal Formation: Sugars

• Describes a broad class of molecules

• Type of carbohydrate

• Simplest is glucose

• Carbs are metabolized in body to glucose (4 cal per gram)

Identify each compounds as either a hydrate, hemiacetal, or acetal.

(far left) acetal because two -OR groups

(middle) hydrate because 2 -OH groups

(far right) hemiacetal because 1 -OR, 1 -OH

How would you classify the following structure?

hemiacetal

Acetal Formation Synthesis Example

Can be used as protecting groups

Nucleophilic Addition of Amines: Imine Formation

NH3 and RNH2 add to aldehydes and ketones to yield imines.

Which option below will result in the following molecule as the major organic product?

Some negatively charged nucleophiles (basic conditions)

HO - (hydroxide ion)

H - (hydride ion)

R3C - (carbanion)

RO - (alkoxide ion)

N (triple bond) C (cyanide ion)

Some neutral nucleophiles (acidic conditions)

HOH (water)

ROH (alcohol)

NH3 (ammonia)

RNH2 (amine)

Nucleophilic Addition of Amines: Cyanohydrin Formation

-CN adds to aldehydes and ketones to yield cyanohydrins.