Organic Chemistry
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- reversible condensation reactions. The products are β-keto esters rather than α,β-unsaturated carbonyl compounds
- to the malonic ester synthesis, but the final products are ketones (specifically derivatives of dimethylketone (acetone))
- The aldol addition is an equilibrium process that generally favors the products for aldehydes, however not necessarily for ketones
- enolate is ambidentate, it can undergo C-attack or O-attack using the O or the alpha carbon as the nucleophilic center
- hydrohalic acids (HX, X= Cl, Br, I), as the halohydrin initially formed often reacts further with HX to give a 1,2 dihalide
- thiol deprotonated by OH to form thiolate ion, thiolate ion functions as a nucleophile and attacks an alkyl halide (good nucleophile turns into a great nucleophile)
- C2O oxirane ring is the parent (O is 1, C's are 2 and 3). substituents named in alphabetical order; lowest possible numbers (1,2-epoxyethane, 3,4-epoxy-4-ethyl-2-methylhexane, 1,2-epoxy-1-methoxypropane
- tertiary butyl group, nucleophile could not get to the electrophile, E2 reaction would produce isobutane
- carbon skeleton can be modified. Make C-C bonds with a carbon nucleophile.can install a two carbon chain between an R group and an OH group
- called sulfides or thioethers, named like ethers. Sulfides can also be named using an alkylthio side group on an alkane parent
- Water or an alcohol (weak nucleophiles) can also be used as the nucleophile in the presence of a small amount of acid catalyst (usually H2SO4)
- with an asymmetric epoxide, the strong nulceophile attacks the least substituted position (SN2)
- by an SN2 reaction involving sodium hydrosulfide (HS-) so primary alkyl halides work best
- like those of alcohols, using the name of the alkyl group with the word mercaptan
- S in the middle of two R groups double bound to an oxygen
- to describe the proximity of atoms to the carbonyl center (which isn't given a Greek letter designation!
- both steric and electronic effects play a role in determining the overall regiochemistry of ring opening with prior protonation
- more reactive than ethers due to the presence of the larger, more polarizable S atom. Unlike ethers, sulfides will undergo attack on an alkyl halide
- alkene + MCPBA gives epoxide plus a carboxylic acid, stereospecific
- two oxygens double bonded to sulfur, two R groups also attached