LECTURE #22 Thurs., Nov.15, 2007
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1 Provide a rxn sequence to make these as the major products Answers: 1. i Pr-Cl, AlCl 3 2. conc. fuming? H 2 S 4 3. Cl 2, FeCl 3 or AlCl 3 4. dilute H 2 S 4 note: normally aqueous workup after step 1, but H 2 S 4 for sulfonation will do it! (not wrong if include step 1b = H 2 ) Cl 1. propionoyl-cl, AlCl 3 2. H 2? 3. Zn(Hg), HCl, 4. CH 3 CH 2 Cl, AlCl 3 5. H 2 1. conc. fuming H 2 S 4 2. propionoyl-cl, AlCl 3? (1) 3. dilute H 2 S 4 note: normally aqueous workup after step 2, but dilute H 2 S 4 for desulfonation will take care of it! CHEM 222 section 01 LECTURE #22 Thurs., Nov.15, 2007 Lecture topics & readings Today s class - continue rxns of carbonyl compounds (Ch.16-18) Before next class - xxxxxxxxxxxxxxxx Next class - continue rxns of carbonyl compounds (Ch.16-18) LAB EXAM: Thurs. Nov.22 1 st 40 minutes of class (+ lecture) (2)
2 Rxns with H-nucleophiles: reduction to RH (17.6, 19.1) Class II - aldehydes & ketones: H - addition (3) Hydride-transfer reagents: Sodium borohydride: NaBH 4 Lithium aluminum hydride: LiAlH 4 (LAH) weaker stronger Violently reactive to H 2! Which reagent? NaBH 4 not reactive enough to donate H to esters, RCH, amides (less reactive than aldehydes / ketones) Procedure: use anhydrous, aprotic solvent 1 st step: add hydride reagent to carbonyl compound solution 2 nd step: aqueous acidic workup (carefully: Lewis acid byproduct) Class I: H - addition + elimination of LG less nucleophilic than H - Acid halides (anhydrides) + Cl - Esters Carboxylic acids Amides Acidic workup would yield ammonium salt (4) Mechanisms similar see 17.6 for differences
3 H - reduction of class I carbonyl proceeds via 2 successive Nu additions Mechanism for ester reduction ( & acid halides & anhydrides): Reagent that stops at aldehyde intermediate: DIBALH For RCH & amides: acidic H s present changes mechanism (5) (not via aldehyde) check it out on your own Rxns with C-nucleophiles: some seen already (17.4, 5, 7) H R Grignard / organolithium (17.4): ANHYDRUS conditions new C-C bond formation: add R group C= reduced to C-H stereochem.: add from either face racemic 1.) R-MgBr, ether 2.) H ) R-C C: - Na + 2.) H 3 + H C C-R Acetylides (17.5): similar to Grignards (6) NaCN, HCl very carefully... Cyanohydrin formation (17.7): new C-C bond: add C N group reversible rxn doesn t occur with esters: Class I, poor LG useful route to other groups: reduce C N to 1 NH 2 (use H 2 /Pt/C) hydrolyze C N to CH (see 16.19)
4 verview: Carbonyl compounds react with NUCLEPHILES Class of Nu C-Nu H-Nu -Nu N-Nu (7) Act like C H Reagents RMgX, RLi RC C: Na + N C: Na + + more exotic ones later NaBH 4 (milder) Reduction: LiAlH 4 (stronger) R-H forms + Class I cmpds also lose their LG H 2, RH NH 3, amines Result when add to C= ADDITIN +/- ELIMINATIN Reduction + framework extension: alcohol + new C-C bond alcohol + new C-C bond (to C CR ) alcohol + new C-C bond (to C N ) Next topic 1 st Class I compounds, then Class II Rxns of esters with & N nucleophiles: if Nu LG. ADDITIN+ELIMINATIN (16.10,12) Basic conditions, Nu = H -, or R - : like acyl halides Hydrolysis: yields carboxylate (& RH) Mechanism: 1. Nu attack by H - 2. Td collapse (3.) H + transfer to R - + acidic workup RCH Transesterification: (switch to different alkoxy group on ester) (8)
5 ( ) Acidic conditions, Nu = H 2, or HR : protonated ester ADDITIN+ELIMINATIN Acid-catalyzed Hydrolysis: yields RCH & RH Mechanism: 1. protonate ester 2. Nu attack 3. H + transfers 4. Td collapse To drive eqm fwd: 1. excess H 2 2. remove product as forms Transesterification: via similar acid-catalyzed mechanism (9) Rxns of RCH with & N nucleophiles: going the other way ADDITIN+ELIMINATIN Push the equilibrium the other direction: Fischer esterification To drive eqm fwd: 1. excess RH 2. remove H 2 as forms Can make ammonium carboxylate salts too: if Nu = amine (10)
6 ( ) Rxns of amides with & N Nus: less reactive 1 st, USEFUL SYNTHETIC RXN - Can dehydrate amides to yield nitriles: Dehydrating agents: 1. P PCl 3 3. SCl 2 More biologically relevant : acid-catalyzed hydrolysis (or alcoholysis) Acidic conditions, Nu = H 2 or HR : addition + elimination Stable in base conditions: - NR 2 > - R - H Won t react unless C= protonated (11) Work through the mechanism on your own: Hydrolysis of a nitrile yields a carboxylic acid (16.19) (occurs in either acidic or basic conditions ) an α-hydroxy acid General mechanism of acid-catalyzed hydrolysis of a nitrile: (12) Don t memorize this one just follow through the logic.
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