Part 6

Process whereby an aldehyde or ketone is reacted with ammonia, a primary amine, or a secondary amine to form a primary, secondary, or tertiary amine, respectively.

Product: Imine Additional reduction with hydrogen in presence of a catalyst (Raney Nickel) = amine.

Product: Amine

Nitrogen double bonded to a carbon and has about the same polarity as a carbonyl functionality.

Good Polar Aprotic Solvent. Therefore, good in SN2 reactions.

Strong nucleophile. Good in SN2 reactions.

Weak base, therefore good leaving group for SN2 reaction.

(4n + 2) pi So, can be 2, 6, 10, etc…

Cl is Ortho, Para-directing, so will attach Cl to para or ortho positions depending on substituents.

Oxidizing agent Change toluene to COOH.

R-groups are Ortho-, para- directing, so nitro will add to ortho or para position.

Aldehydes and ketones can be completely reduced to alkanes by this metho. The carbonyl is first converted to a hydrazone, which releases molecular nitrogen when heated and forms an alkane. Only useful under basic conditions. (use H2NNH2/Base/heat)

Where an aldehyde or ketone is heated with amalgamated zinc in hydrochloric acid.

Grignard reagents (RMgX) add to the carbonyl groups of ESTERS to form KETONES; however, the ketones are more reactive than the initial esters and are readily attacked with more grignard reagent to make TERTIARY ALCOHOLS.

Important reaction of ESTERS. Simplest case: two moles of ethyl acentate react under basic conditions to produce a beta-keto ester. Also called teh acetoacetic ester condensation. Enolate ion of one ester acts as a nucleophile, attacking another ester.

RMgX (equivalent to R- nucleophile)

When a different alcohol attacks the ester, the ester is TRANSformed, and TRANSesterification results. (ester into another ester)

Answer: amide + alcohol Nitrogen bases such as ammonia will attack the electron-deficient carbon atom, displacing alkoxide, to yield an amide and an alcohol side product.

Converts amides to primary amines with the LOSS of the carbonyl carbon. Involves the formation of a nitrene (nitrogen analog of carbene).

Amides can be reduced with LAH to the corresponding AMINE, but NO carbon is lost.

Oxidation reagent. Will reduce to carboxylic acids.