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1) Aldehyde 2) Ketone 3) Alcohol 4) Alkene/ Alkyne/ Benzene 5) Ether/ Alkane/ Haloalkane |
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have leaving group carboxylic acid derivative
Carbox Acid, Ester, Amide, Acylhalide |
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no leaving group
Aldehyde, Ketone |
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Single C Carbonyl on ring |
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*Aldehyde always C-1 *drop e- and -al |
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*Drop -e, add -one *=O x2 = -oxo group |
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Electron Withdraw Substitution |
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*Major mechanism aldehydes and ketones *Acid/ Base |
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*Nu- *Base catalysts *anion 1)Nu- attack 2) protonation |
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Nu-H neutral *acid catalst *cation H+ already present 1)Protonate 2) Nu- attack |
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*Major new Nu- for carbonyls *Gringard: Mg *OrganoLi: 2Li, THF |
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*Nu-H *Can make H- *2 Types: LiAlH4, NaBH4 |
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*less reactive *works with alcohol as H+ donor in place |
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*more reactive *H3O+ after to add H+ |
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*Forms by Nu- Acyl Add to C=O w/ CN- or HCN *Good way to add Nitrile to molecule |
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Hydrogenation of Cyanohydride |
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Hydrolysis of Cyanohydire |
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*Good Nu- Form 1) Imine- 1 amine 2) Enamine- 2 amine |
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*react with H2O to reform C=O *reversible |
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Connect Imine/Enamine to Amine |
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*Use reduction *Pd/H2, NaBH3, CN(pH2) |
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*product of H2O to C=O via Nuc Acyl Addn *AKA hydration of carbonyl *form from carbonyls in aq soln *exist as equill, can't isolate |
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Better E+ attracts more H2O more inc % |
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use ROH *single addn with carbonyls *hemiacetal |
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any amount of ROH + conj base |
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cyclic can be isolated b/c solv not part of rxn |
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*Neutralizing acid * Freeze in place *No reverse w/o H+ |
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Acetal: Strongly Basic Nu- |
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*tend to 1,2 addn *react @ C=O *pKa -25 *goes to largest part+, irreversible *RMgBr, RLi, LiAlH4, NaBH4, C=C- |
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*1,2 addn *react @ B-Carb *pKa- 25 *go to largest part+, reversible |
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*good res struct *low E *stabalize - |
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add 2nd C=O 1,3 dicarbonyl |
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*allow for tautomerization *rearrangement *equill between C+O + enol *good Nu- w/ enols + Carbonyl |
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Phenol prefers enol b/c aromatic ring |
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C=O + Base + E+ (Base/ E+ or 1)base 2)E) |
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E+: go to C H+: go to O (taut) |
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lots of time weaker equillibrium base NaOH |
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faster stronger base NaH2, NaH on hindered base LDA |
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Lithium Diisoprpyl Amide (LDA) |
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strong hindered base means deprotanate |
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