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Organic Chemistry
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- the hydroxide ion (strong nucleophile) attacks the carbonyl group (electrophile). Protonation of the intermediate gives the hydrate
- R2B-H over H2O2 and NaOH gives antimarkovnikov addition resulting in an aldehyde
- aldehydes are generally more reactive than ketones (sterics and electronics)
- two equivalents of an alcohol (weak nucleophile) will react with an aldehyde or ketone to give an acetal
- O3 over DMS gives two ketones, cleaves a double bond
- the unhydrated keto form (carbonyl) more than for aldehydes (aldehydes are more reactive)
- the enolate typically constitutes only a small fraction of the equilibrium mixture
- more reactive than a ketone (the enolate anion formed on deprotonation (conjugate base) is stabilized by the electron-withdrawing halogen
- LDA (or NAH... H2 product) can convert a carbonyl compound completely to its enolate, avoiding an equilibrium mixture of carbonyl compound and enolate
- in the presence of a strong base from an aldehyde or ketone.
- The trihalomethyl ketone reacts with hydroxide ion to give a carboxylic acid. A fast proton exchange gives a carboxylate ion and a haloform
- attack by the enol form of the ketone on the electrophile halogen molecule. Loss of proton gives the haloketone and the hydrogen halide
- Stork enamine synthesis (Michael addition) gives 1,5-difunctionalized product
- a nucleophilic enolate anion, which then attacks the electrophilic halogen molecule
- substrates with different kinds of α-H's are used; LDA gives side reactions with aldehydes, and so they are unsuitable here
- Claisen condensations give beta keto esters (1,3) , uses NaOCh2CH3 over H3O+
- identical partners, while crossed/mixed aldol reactions involve different reactants
- the alkyl halide, and the resulting diester can be hydrolyzed to the dioic acid under either acidic or basic conditions
- alkylation of enolate ions, aldol reactions compete, base can attack alkyl halide (SN2/E2)
- NaOH over H2O, aldol addition gives a beta-hydroxy aldehyde or ketone