09-11 - 9/11/2009 Predict the more acidic compound. Draw...

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Unformatted text preview: 9/11/2009 Predict the more acidic compound. Draw both products and their resonance structures. Which of the following C=O compounds is more stabilized by resonance? O O N H H H C N H + H H3C O C CH3 H3C O C CH3 A H C A O H C N H H3C O C O CH3 non octet structures O H3C C O CH3 H3C O C O CH3 B H H H C N H H H H H C N H 1 B + H octet structures Which of the following C=O compounds is more stabilized by resonance? Which of the following C=O compounds would be predicted to react faster with methyl lithium? O H3C C CH3 H3C O C CH3 A A O H3C C O CH3 H3C O C O CH3 H3C O C O CH3 H3C O C O CH O C = R O C R not H3C O C CH3 B B Which of the following C=O compounds would be predicted to react faster with methyl lithium? Which of the following C=O compounds would be predicted to react faster with methyl lithium? O H3C C CH3 H3C O C CH3 A A E O H3C C O CH O C + Li CH3 O C CH3 energ energy E Li H3C O C O O C + Li CH3 O C CH3 Li CH B B reaction reaction 1 9/11/2009 Which of the following C=O compounds would be predicted to react faster with methyl lithium? Li O CH3 + Li CH3 H3C C CH3 Organic Chemistry, Ch 2 What is Organic Chemistry? who we are NH2 HO OH N H serotonin HO O ascorbic acid OH OH what we eat O H3C C resonance st stabilization O H3C C O CH + Li CH3 A CH3 no resonance st stabilization Li O H3C C O CH3 O B CH3 pentacene what we use Organic Chemistry, how can it be organized? Organic Chemistry, how can it be organized? H amines —NH2 NH2 HO alkanes C C NH2 HO N H alcohols —OH N H aromatics 10 Organic Chemistry, how can it be organized? H amines —NH2 alkanes C C alcohols ethers aldehydes —OH —O— hydrocarbons alkenes C C C H =O ketones C C =O aromatics carboxylic acids C =O amides C =O 11 12 OH many others!! NH2 2 9/11/2009 Why organize organic chemistry around Functional Groups? amines —NH2 alkanes H C C alcohols —OH hydrocarbons alkenes C C aromatics NH2 HO H H H HO 13 N H cholesterol serotonin 14 Why organize organic chemistry around Functional Groups? O HO R + R C Cl R O C O R + H Cl The HO- functional group in different molecules will actually have slightly different reactivities. alcohol acid chloride O ester O H O CH3 + H Cl H H OH H OH H HO CH3 + CH3 C Cl CH3 C methanol acetyl chloride methyl acetate HO H O H HO H+ CH3 C Cl O CH3 C O H H H HO H H H H H H cholesterol acetyl chloride cholesteryl acetate cholesterol 16 With respect to the environment of the HO group which of the following alcohols, A, B or C, is most like cholesterol? 1° carbon atom 2° carbon atom 3° carbon atom Functional Groups and Organic Synthesis alkane CC C H H H C OH H H C C C OH C O C A B HO H C C H H C H H = R O C R not H3C O C CH3 O H C H O C = R O C R not O C or C C HO H C cholesterol C 17 18 3 9/11/2009 Functional Groups and Organic Synthesis alkane CC Choose the next best resonance structure for each of the compounds shown below. alkane CC O C Li C i ii A. A. i + iv B. i + iii O C Li C R CH3 R = Li C R not O C Li C Li C CH3 C. ii + iv D. ii + iii CH3 O C Li C iii 19 iv 20 Predict the product of the following reaction. alkane alkane CC Li O C C Predict the product of the following reaction. alkane CC Li O C + Li C O C C O C + Li C Li O C C H H O H O C + Li OH C How are organo metallic compounds prepared? organolithium Li C Br C How are organo metallic compounds prepared? organolithium Li C Br C reduction = gain of electrons. oxidation = loss of electrons Li Li O C + Li C + Li Br O C C H H O H O C + Li OH C O C + Li Li Li O C + Li Br C C H H O H O C + Li OH C In the above reaction is the carbon atom: (A) oxidized or (B) reduced? 4 9/11/2009 How are organo halides compounds prepared? organo bromine Br C H Br C Br O H Li Li O C + Li C + Li Br O C C H H O H O C + Li OH C C H O H C H O H C + Br How are carbonyl compounds prepared? carbonyls O=C O=C H Br C Br O H Li Li H O + Li C + Li Br C C H O H O C + Li OH C C HPy CrO3 O C OH C H How are carbonyl compounds prepared? carbonyls O=C Carbon-carbon bond forming reactions are very important for converting simple organic compounds into complex organic compounds! reduction = gain of electrons. oxidation = loss of electrons H Br Li OH C H HPy CrO3 O C + Li C + Li Br O C C H H O H O C + Li OH C O C + Li C H H O H O C C In the above reaction is the carbon atom: (A) oxidized or (B) reduced? HPy CrO3 Functional Groups and Organic Synthesis. Other reactions. Functional Groups and Organic Synthesis. Other reactions. alkenes CC H C C Br OH C C + H2O + Br hydrocarbon CC l H l H C C H2 Pd/C C H C H 29 hydrocarbon CC l H l H C C H2 Pd/C C H C H 30 5 9/11/2009 Functional Groups and Organic Synthesis alkenes H OH C C Br C C hydrocarbon C C H2 Pd/C C H C H H carbonyls C OH PCC C O haloalkane C OH H Br C Br alkane C Li 1. C O 2. H2O Li C C OH organolithium C Br C Li 31 6 ...
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