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orgo 4/30 pt 2
| Question | Answer |
|---|---|
| ethylene glycol, acid | forms a cyclic acetal-like ring; the product is a protected carbonyl-style cyclic structure rather than the open-chain diol |
| appropriate alkyl halide / alkoxide combination for ether formation | makes an ether by replacing a leaving group with an oxygen-containing group |
| acid plus heat for making ethers from alcohols | gives an ether, often with a simple alcohol group becoming part of the new ether bond |
| NaOH, H2O with a strained epoxide | opens the epoxide ring and gives a larger, more open alcohol product |
| OsO4, then workup | turns an alkene into a diol, adding two OH groups to the same side |
| B2H6 / diglyme, then H2O2 / NaOH | changes an alkene into an alcohol with the OH on the less substituted carbon |
| CH3CO3H, then NaOH / H2O | converts an alkene into a diol through epoxide formation and opening |
| CH3CH2MgBr, then H2O | adds an ethyl group and opens ethylene oxide to make a longer primary alcohol |
| CH3OH, H2SO4 | adds methoxy under acidic conditions, giving an ether-type product |
| CH3MgBr, ether, then H3O+ | adds a methyl group to a carbonyl and gives a more substituted alcohol |
| H2O, HgSO4, H2SO4 | changes an alkyne into a ketone |
| benzene + 2-methyloxirane, AlCl3 | opens the epoxide and gives an alcohol-containing aromatic side chain product |
| K2Cr2O7, H2SO4, H2O | turns a secondary alcohol into a ketone |
| H2O, HgSO4, H2SO4 | turns an alkyne into a ketone |
| O3, then H2O | cuts a double bond into smaller carbonyl fragments |
| LiAlH4, then H2O | reduces carbonyl-type functional groups to alcohols |
| H2, Lindlar catalyst, then H2SO4, H2O | partially reduces an alkyne first, then gives a ketone after hydration |
| H2O, H+ | hydrolyzes protecting groups like acetals back to the carbonyl compound |
| excess CH3OH, catalytic H2SO4 | converts an aldehyde or ketone into an acetal, which protects the carbonyl and replaces the C |
| H2O, H+ on a nitrile | converts the nitrile into a carboxylic acid |
| H2O, H+ on an ester | converts the ester into a carboxylic acid plus an alcohol |
| H2O, H+ on an acetal | removes the protection and restores the aldehyde or ketone |
| H2SO4, alcohol, heat | makes a Fischer esterification product; the acid and alcohol become an ester plus water |
| acid hydrolysis of a cyclic acetal | breaks the ring and regenerates the original carbonyl compound |
| H2SO4, alcohol | Fischer esterification, turning a carboxylic acid into an ester |
| H218O, HCl | exchanges oxygen in the carboxylic acid under acidic conditions |
| aqueous acid on a nitrile | converts the nitrile into a carboxylic acid |
| method for benzoic acid from an alkyl benzene side chain | oxidizes the side chain all the way to a carboxylic acid |
| method for cyclopentanecarboxylic acid from bromocyclopentane | forms a carboxylic acid only if the carbon skeleton is built correctly first |
| method for 2,2-dimethylpropanoic acid | changes the starting group into a carboxylic acid without changing the carbon framework |
| lactone-forming hydroxy acid | cyclizes to form an ester ring and loses the open-chain acid/alcohol form |