L16a - How? Devising organic synthetic schemes H Last...

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1 1 © Kay Sandberg How? Devising organic synthetic schemes HO alkane alcohol HH H H H anti-Markovnikov 1. BH 3 -THF 2. H 2 O 2 ,NaOH HO H H H H Br 2 Δ ,h ν H Br NaOCH 2 CH 3 HOCH 2 CH 3 2 ©Dr. Kay Sandberg Last lecture This lecture Alkene reactions Chirality 2) hydroboration-oxidation 3) vicinal dihalide formation 1) acid catalyzed hydration 4) vicinal halohydrin formation 5) epoxidation 6) ozonolysis 3 O O O O O O Section 6.19 alkene © Kay Sandberg Resonance structures of ozone Alkene - Ozonolysis C C C C O + O 3 OO ozone ozonide “lysis” is a root that can mean “to break apart.” 4 Section 6.19 hydrolysis © Kay Sandberg Alkene - Ozonolysis C C C C O + O 3 2 carbonyl compounds O C C C O + H 2 O C O + + H 2 O 2 alkene cleavage reaction ozonide Step 1 Step 2 2 equivalents of a ketone symmetric alkene (tetra-sub) 5 Section 6.19 ketone © Kay Sandberg Various carbonyl compounds O R R O R H O R OH O aldehyde carboxylic acid formaldehyde 6 Section 6.19 © Kay Sandberg Alkene - Ozonolysis C C ketone ketone C C O O Short cut visualization Slice Slide Slap 1. O 3 2. H 2 O 4-heptanone 2-butanone
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2 7 Section 6.19 © Kay Sandberg Alkene - Ozonolysis C C H 1. O 3 2. H 2 O, Zn aldehyde ketone O C H C O 1. O 3 , HOCH 3 2. (CH 3 ) 2 S or 1. O 3 2. H 2 O, Zn 8 O C O H ketone C O Section 6.19 © Kay Sandberg Alkene - Ozonolysis C C H 1. O 3 2. H 2 O Carboxylic acid 9 O C H H ketone C O CH 2 CH 3 CH 3 Section 6.19 © Kay Sandberg Alkene - Ozonolysis C C CH 2 CH 3 CH 3 H H 1. O 3 , HOCH 3 2. (CH 3 ) 2 S formaldehyde 10 Section 6.19 © Kay Sandberg Alkene – Ozonolysis: conditions and results C R R 1. O 3 2. S(CH 3 ) 2 (or Zn) C R H C H H 1. O 3 2. H 2 O O C R R O C R R O C R H O C R HO O C H HO O C H H SM alkene (SM=starting material) ketone ketone aldehyde carboxylic acid formaldehyde formic acid 11 Section 6.19 © Kay Sandberg Alkene - Ozonolysis 1. O 3 2. H 2 O O ketone Draw the skeletal structure of the reactant alkene ketone O 12 © Kay Sandberg Section 7.1 Stereochemistry C C H Br Br H C C H Br H Br Br Br Br Br 1,2-dibromoethene Stereoisomers 1,2-dibromocyclopentane trans cis ( Z
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L16a - How? Devising organic synthetic schemes H Last...

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