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by: Ashley Kunze


Ashley Kunze
GPA 3.61


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About this Document

Class Notes
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This 4 page Class Notes was uploaded by Ashley Kunze on Thursday October 22, 2015. The Class Notes belongs to CHEM 109B at University of California Santa Barbara taught by Staff in Fall. Since its upload, it has received 69 views. For similar materials see /class/226949/chem-109b-university-of-california-santa-barbara in Chemistry and Biochemistry at University of California Santa Barbara.

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Date Created: 10/22/15
CHEM 109B CLAS Sp09 Reactions of Carbonyl Compounds n u 0 U 0 O R 039 pyrHCl gt pyr R o R o o H H o pyrHCl A pyr R oH Reactivity Carbonyl Compound R c O O H R i pyrHCl pyr R OR O X NH N39HR N39R z amme orpyrHCl Orpyr R NHZ EIC O O H H 2 gt R OH O O O O O H R gt R OR R OH O 0 XS N39Hg NHR NR 2 amme orpyrH gt orpy R NHZ EIC R OH i N 1 C N HO cyamde lon gt 2 Hgo H20 H H R 1 39cciR Ho acetyhde lon gt 2 Hgo H20 H H 0 MB 1 R E r H Gngnard magmt R gt 2 Hzo H20 H H H2 laamme O 2 H H H30 R R PH 2 0 W P R P0 W RH reduction rxns Page 1 of5 CHEM 109B CLAS Sp09 Reactions of Carbonyl Compounds Reactivity Carbonyl Compound quot 39CEN Ho N We gt 2 Hgo H20 H P R 1 1330 Ho acetyhde 1on gt 2 Hgo H20 H R Ma 1 R Er o Gngnard magmt X gt 2 Hzo H20 H R HOH HO OH H30 or39oH H R O 0 PO A H R XOR P H H30 or39OH H R R1 N P N 1 aman 0 2 k H H H20 H P N R P R 2 amme N HOH H30 R H R PH 2 R CR W P R 0 PH gt PM PH H R W reduction rxns 1 39CEN Ho N cyamde 1on gt 2 Hgo H20 H H R 1 39CECiR Ho acetynde 1on gt 2 Hzo H20 R R Ma 1 R Er Ho Gngnardreagmt R gt 2 HoHzo P O R A o P P H Ho or39oH HO 1 H30 or39OH H Ni 1 amme H20 P P Page 2 of5 CHEM 109B CLAS Sp09 Reactions of Carbonyl Compounds Reactivity Carbonyl Compound H N R R R R 2a amine N HOH Hgot R2R R PH 2 RCR PH R PO PH gt Ph R R p reduction rxns 0 XS 0 H H R OH gt Hgot catalyst or base promoted O O as o H RH R OH r a H 0R F OR H30 catalyst orbasepromoted O stH3NHR N39R 2 ROH R NHZ EIC reductlon rxns O xs 0 H R H20 R OR o Hzot catalyst i or base promoted R OH 0 x5 N39Hg N39HR gt R O39N39HA etc 0 O H H amine gt HClht R 0 o o o o O H R amine gt t R NHz R NHR R W HClht R 0R P205 Poc13 soc12 o gt R iiw H H ht reduction rxns Three possible mechanisms for Nuc attack on carbonyl carbon Page 3 of5 CHEM 109B CLAS Sp09 Reactions of Carbonyl Compounds Nua j 1 OHurZ o H or z R v lt R v gt V39 R Nu Nu Nu Addition Tetrahedral Intermediate Substitution R v T H20 Nu Condmsanon Reacting aldehydes and ketones with nitrogen Nucs AdditionElimination reactions 0 H H 1 NH2 a reducing agent X N gt H20 PdC R RurH H H R El H ammonia laamme R o H N i N A H20 R mm H R R RmrH laamme imme R R R urH R gt33 H my R R RurH 2 amme enamin oH N O H uaceHgot i N 2 H H20 R RurH H OH R RurH hydroxylamme oxime NH 2 O H N uaceHgot H20 N R RurH H W 39 R RurH hydrazine hydmzone Ho39180 c Z I NE 5 R RnrH H NHZ NH I I Wm WolffKlshner Reductlon NHPH O H N A mceHgot H20 R WurH H H R urH phenylhydmzine phEnylhydrazone Page 4 of5


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