Ketones, Aldehydes CH21 PS CLASS. Recall the many times we’ve synthesized these! I command thee. Oxidation of R-OH – (Periodinane, CrO 3 /Na 2 Cr 2 O.

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Presentation transcript:

Ketones, Aldehydes CH21 PS CLASS

Recall the many times we’ve synthesized these! I command thee. Oxidation of R-OH – (Periodinane, CrO 3 /Na 2 Cr 2 O 7 ) Hydration of Alkynes (keto-enol tautomerism) – H 3 O+/HgSO 4, BH 3 /H 2 O 2, OH-, etc… Friedel-Crafts ACYLation of Aromatics – (acid halide + AlCl 3 )

REACTIONS OF ALDEHYDES/KETONES Oxidation of Aldehydes Nucleophilic Additions (overview) – Hydride (H-) and Grignard (R-) as Nucleophiles – Water addition (hydrate/diol/geminal diol formation) – Alcohol addition (acetal formation) – Amine addition (imine formation) Conjugate Nucleophilic Addition Reactions

Major Synthesis

Oxidation of Aldehydes Where [O] = CrO 3 among others.

Nucleophilic Addition Rxns Slightly different mechanisms in acid or base. Neutral vs. Negatively charged Nucleophile General picture (basic):

Reactivity Notes: Less steric hindrance with aldehyde Benzaldehyde less reactive due to resonance stabilization.

Reduction of Ketones/Aldehydes

Addition of Grignard Reagent

Grignard Reagents + carbonyls

Practice! COME UP WITH PAIRS, More than one answer for some.

Practice!

Hydrate formation/ Geminal Diols

Basic vs. Acidic BASIC: Strong nucleophile attacks, as in Nu- ACIDIC: Carbonyl is converted to a stronger ELECTROPHILE as CABON BECOMES MORE POSITIVE.

Problem

Acetal formation ACID CATALYZED… AGAIN, CARBONYL MADE INTO BETTER ELECTROPHILE.

Acetal Formation

2 alcohols/ 1 diol can be used to ‘protect’ an aldehyde or ketone from a reaction.

Nuc. Addition of Amines to form: Imines Amine must have 2 protons, RNH 2

If amine is 2° we form enamines

Practice addition of amines:

Problems Predict the Products!

Problems

Wittig reaction, addition of R: - to C=O forming C=C Limits of SN2???

Addition of ylides

Exercises

Conjugate Nucleophilic Addition Rxns

THE DOUBLE BOND IS EFFECTIVELY “POLARIZED” INTO A NEGATIVE REGION THAT’S RESONANCE STABILIZED, AND A POSITIVE REGION AT THE BETA-CARBON.

Predict the product + HCN

Practice

Predict the Products a.NaBH 4 /H 3 O+ b.NH 2 OH/HCl c.2 CH 3 OH /acid d.CH 3 MgBr then acid

Predict the Products NaBH 4 /H 3 O+ NH 2 OH/HCl 2 CH 3 OH /acidCH 3 MgBr then acid

Predict the Products NaBH 4 /H 3 O+ NH 2 OH/HCl 2 CH 3 OH /acidCH 3 MgBr then acid

Exercises

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