Week+2+Handout (3)

Week+2+Handout (3) - For Problems 1-6, draw the structure...

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Week 2 Handout CHEM 35 Sections 6, 9 and 16 TA: Brian Loy Aldehydes and Ketones: Carbonyl Addition Reactions The reactivity of the carbonyl group is driven by its polarity: The characteristic reaction of carbonyl compounds is nucleophilic addition at the carbonyl carbon: Reactions with Strong Nucleophiles: 1) Organometallics: organomagnesium and organolithium compounds 2) Hydride reducing agents: LiAlH 4 and NaBH 4 3) Wittig Reagents Reactions with Weak Nucleophiles: 1. H 2 O C O C O = C O δ + δ - C O δ + δ - Nu C O Nu C O 1. R-MgBr 2. H 3 O + (acid workup) 2. H 3 O + (acid workup) 2. H 3 O + (acid workup) 2. H 3 O + (acid workup) 1. RLi 1. LiAlH 4 1. NaBH 4 Ph 3 P=CR 2 OH R OH R OH H OH H C C R R Alcohol Alcohol Alcohol Alcohol Alkene
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2. R-OH (acid or base catalyzed) 3. R-NH 2 (where R = H or alkyl group) 4. - CN The best way to learn is by practice!
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Unformatted text preview: For Problems 1-6, draw the structure of the organic product in the box. There should be no charges on ANY atom. 1. 2. C O C O C O C O C O C OH HO C OR HO C OR RO C N R C CN HO-CN R-NH 2 R-OH R-OH H + (acid)-OH (base) H 2 O Cyanohydrin Imine (R = H) or Schiff Base (R = alkyl group) Acetal Hemiacetal Hydrate O CH 3 CH 2 CH 2 CH 2 NH 2 PPh 3 C H Ph C C H H C O H CH 2 Cl 2 3. 4. 5. 6. 7. Using good arrow notation and drawing the structures of all intermediates, give the mechanism of the following reaction. O NO 2 Excess CH 3 CH 2 OH H 2 SO 4 O 1. KCN 2. H 3 O + (acid workup) H O + MgBr O O 1. LiAlH 4 2. H 3 O + (acid workup) O H O O HOCH 2 CH 2 OH H +...
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Week+2+Handout (3) - For Problems 1-6, draw the structure...

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