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22 Cards in this Set
- Front
- Back
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nucleophilicity series |
-CH2R>-NH2R>-OR. then OH>NH3>cooh>water increased nucleophilicity is associated with decreased electronegativity. they want to share electrons, not hog. good nucleophile is a bad leaving group. |
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leaving group |
part of molecule that leaves. a good lg is a bad nucleophile, and a good lg is stable in solution. good lg's are often atoms with a greater number of electrons shells, as they can distribute their charge. |
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electron donating groups |
-OH, -O-, -NR2 -O-R -R |
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Electron withdrawing groups |
-N+O2, -NR3, CCl3 anyting with a partial positive charge. and halides |
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alcohol acidity trend |
More Electron withdrawing groups means more basic. they stabilize the positive charge. More Electron donating groups means more acidic. they stabilize the negative charge on conj base. they also make the partial positive charge on the acid more positive and unstable. tertiary alcohols are the least acidic whiche methyl alcohol is the most. more ED G means more basic, less acidic. |
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sulfonates |
tosylates and mesylates. tget have many bonds to due the dorbitals i sulfer. they have a lto fo distribution of charge, so they are weak bases and good leaving groups. used to protect alcohols. |
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ethers. |
cant hydrogen bond by it self, but can with NOF-H compounds. relatively non reactive, good choice solvent for organic reactions. |
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amine
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good nucleohpile. can take on fourth bond and become positiviely charge as well. |
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stereoselective |
one chiral product is preffered. stereospecific means 100 percent of the product is one chiral product. |
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carbonyl rectivity trend |
acid halide>aldehyde/ketone>anhydrides/esters>COOH>amide |
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Aldehyde acetal ketal business explain |
Aldehyde- Forms a hemiacetal and then an acetal. Hemiacetal has an OR and an OH. Acetal has two OR. |
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reducing agents |
LAH, very strong. full reduce to cooh/ester/acetate to an alcohol. NaBH4 i guess only reduces a bit. NaBH4 can only reduce ketones and aldehydes, not COOH or esters. |
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oxidizing agents. |
MnO4, CrO4, Cr2O7. oxide alcohols all the way to COOH. PCC is gentle, only oxideze primary alcohols to aldehydes and secondary alcohols to ketones. decarboxylation is the oxidation of a cooh to CO2. Works better when beta carbon is a carbonyl. think back to biochem reactions. |
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aldol condensation |
alpha carbon attacks the carbonyl. aldol has an alcohol and an aldehyde. |
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addition reaction |
does not occur with carboxylic acids, but common in ketones/aldehydes. reverse is also true. ketones/aldehydes don't typically undergo substitution, but COOH does. |
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Alpha carbon hydrogen, next to carbonyl carbon |
the most acidic on an aldehyde |
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benzene ring activation/deactivation |
EWG's deactivate. Like NO2 |
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ring formation which carbon oxygen attacks the carbonyl. 1-6 |
5 attacks. this leaves that CH2OH group which was carbon 6. |
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gabriel synthesis |
phthalimide and diethylbromobalonate combine with base to make an amino acid. The amino acid comes from an R-Br. |
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lipogenesis |
formation of lipids from glycerol and fatty acids. OH's glycerol act as the nucleophile attackin the COOH |
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lipolysis |
lipid breakdwon into fatty acids and glycerol. if it is base catalyzed, it is called sponification. makes soap. |
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melting point fatty acids |
Unsaturated fatty acids have less hydrogens, and thus a lower MW. thus their MP is lower. kindof. just makes it easier to remember. saturated are straight, no kinks. so they solidify easier. |
