Practice final exam - P age o f 1 6 2 1. ( 50p oints) l n t...

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Page 2 of 16 1. (50 points) ln the answer box for each part of this question, draw the expected organic product(s) formed in the following reactions. Be sure to specify stereochemistry, using realistic perspective when necessary, (a) 1. NaNHz, NHg (liq) 2. CH3CH2l N -bromosuccinim ide (c) cH3cH2cH2sH (2 equiv) (1 equiv) LY"' ct/\'v (b) ut2 Ph (d) --\-""" HBr dibenzoylpe roxide 1 . Li, ether (e) 2. H3O* continued. .. next page
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Page 3 of 16 1. (continued) In the answer box for each part of this question, draw the expected organic product(s) formed in the following reactions. Be sure to specify stereochemistry, using realistic perspective when necessary. PBr3 (f) cHso (s) (h) U6nq-U-UFl TsO HBr (catalytic), HrO 2. H2O2, NaOH (pyridinium chloro- chromate) LiCN et"J' (i) THF r\ LJ \,/ | |3
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rage 4 of 16 2. (18 points) Complete the missing structures in the boxes for parts (a) and (b) shown below. It is only necessary to show one enantiomer of each product, but be sure all stereochemistry clearly. cH"cH2 ,cHg (a) -tr< H cD3 peracid (e.9. MCPBA) Hg(OAc)2-H2O NaBH4, NaOH-H20 lr +- H*, CH3OH CHr-C=C-MgBr then H3O+ H2, Pd/C (b) t^. I excess ut2 cn,cr, - { t.oru.nll
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Paoe 5 of 16 3. (28 points) Use the space given to write out a specific sequence of reactions and reagents you would use to carry out each of the following transformations. Show each intermediate clearly. OHH (a) (b) c6Hs-c-c-cH2oH coHsl\.,\ continued. ..
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3. continued. .. Page 6 of 16 cH2-F (c) CH" I H.c-A. ..-/rcHroH "l ,-,. .&""' /'- lJ \,/ | |3 v| |? (d) a\ lJ vr 13
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Paoe 7 of 16 4. (20 points) (a) The mass spectra of 2-ethylcyclohexanone and 3-ethylcyclohexanone, both isomers of C8H140, are shown below. Which is which? In each box, draw the structure that fits the soectrum to the left of it. (b) The C=C stretching frequencies of three alkenes are listed below. Circle below whose alkene has the highest bond dissociation energy: /T LJ \,| |2 vt t2 F.r, 1780 cm-] 1670 cm-l (c) Would you expect the C=C stretching frequency for the hydrocarbon allene H2C=C=CH2 to be higher, lower, or about the same as of a typical alkene at ca. 1 600 cm-l?
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This note was uploaded on 02/11/2010 for the course CHEM 3590 at Cornell University (Engineering School).

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Practice final exam - P age o f 1 6 2 1. ( 50p oints) l n t...

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