13th&14_th_lecture_Ch4_9_28&30_2011(1)

13th&14_th_lecture_Ch4_9_28&30_2011(1) -...

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Draw the Newman projection of the following exact conformation, looking down the C 2 -C 3 bond. C 2 is attached with the OH group, C 3 is a CH 2 group. Are these two molecules the same or different? O H H H OH 1
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Did you get it right? 1 2 3 0% 0% 0% 1. Yes 2. No 3. I did not know how to approach. 2
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Draw SIX Newman projections of the following molecules. Or Draw the most stable Newman projections of the following molecules Or Draw the energy diagram showing the conformations (using Newman projections ) for the following two molecules. Rotate the C2-C3 bond. O H H H OH Looking down the C 2 -C 3 bond. C 2 is attached with the OH group, C 3 is a CH 2 group. Are these two molecules the same or different? 3
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Which is more stable? A or B 1 2 0% 0% 1. A 2. B CH 3 CH 3 C H 3 CH 3 CH 3 C H 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 OR OR B A 4
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CH 3 CH 3 CH 3 CH 3 OR B A possible, easy b o n d c o n n e c t i o n impossible How does this work? 5
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1 2 4 5 6 3 7 8 1 2 3 4 5 6 7 1 2 4 5 6 3 7 8 A B possible, easy b o n d c o n n e c t i o n impossible How does this work? 6
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CH 3 CH 3 CH 3 CH 3 OR B A How does this work? More stable Less axial-axial C-C interactions 7
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Chapter 4 Alcohols and Alkyl Halides ROH,  RX X= F , Cl, Br, I RF is quite different than other RX. 8
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Functional groups Saturated hydrocarbons are relatively unreactive although they can be used as fuels. Other structural units in a molecule exhibit a set of characteristic behaviors under more diverse set of conditions. 9
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ROH R OH R OH R R OH R R RX R Cl Br R Br R ROR' R OR' R O R" Alkene (olefin) Alkyne Alcohols Aromatics Ether Alkyl halide 10
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RNH 2 R NH 2 R NH R R N R R RCOR' R OR' O R R' O RCOOR' R H O RCHO R N H O RCONRR' R R N O R R RSH RSR' RCN N R RCOOH R OH O Amine Primary secondary tertiary Ketone Amide (all protein contain lots of this bond) Ester (perfumes) Aldehyde (used for preserving dead body) Thiol Thiol ether Some others Carboxylic acid Some others 11
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Constitutional Isomerism in  Functional Groups • Different functional groups may have the same formulae, and therefore can be constitutional isomers CH 3 CH 2 O CH 2 CH 3 CH 3 CH 2 CH 2 CH 2 O H diethyl ether butanol As long as they fulfill the octet rule, many others exist. 12
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- Name the alkyl group and the halogen as separate words ( alkyl + halide ) CH CH 3 F F CH CH 3 CH CH 2 CH CH 2 CH CH 2 CH CH 2 Cl Cl Methyl fluoride Methyl fluoride Pentyl chloride Pentyl chloride Cyclohexyl iodide Cyclohexyl iodide H H I I Nomenclature of Alkyl Halides   13
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CH 3 CH CH 2 CH CH 2 CH CH 2 CH CH 2 F F CH CH 3 CHCH CHCH 2 CH CH 2 CH CH 3 Br Br 1-Fluoropentane 1-Fluoropentane 3-Iodopentane 3-Iodopentane 2-Bromopentane 2-Bromopentane CH CH 3 CH CH 2 CHCH CHCH 2 CH CH 3 I I Nomenclature of Alkyl Halides - Name as halo-substituted alkanes. - Number the longest chain containing the halogen in the direction that
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13th&14_th_lecture_Ch4_9_28&30_2011(1) -...

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