prac2sol - I Chem 118C / W / 09 / Nambiar/ Sample Test-2...

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Unformatted text preview: I Chem 118C / W / 09 / Nambiar/ Sample Test-2 Draw the structure of the expected organic product (5) formed in the following reactions. Unless mentioned otherwise, you can assume that all reagents are present in excess. If no reaction occurs, write "No Reaction“. 1.13 Ihv , a, - web! 1. C6H5—CH2—CH3 ‘2 . (5 H5 C 11 L; 2. NaOl-IV l. NaCN; 2. LiAll-I4 2) R-CHzBr (; 3. H20 1 , e 4/ LCH31 .. our,“ 4» 3) CH3-CH2—CH2-NH-CH3 CD HJ {if ‘ . Di 9) 2. AggO/H20/A a 14 OH ' -’ a I :1 © (CH3CO)2O (1 eq)/H20/A 1:? + C429 4) J 65% NHZ Br ' . l.NaNHz/_NH3 3 ¢ ' CH3 P/ Biz 6) CH3COOH , 7) L1 4% «WA. 'AlH4 ’ o _ - _ CH3CH2C0NH2 ’CH§ a, A 2. H20 ‘3 II; . ‘ _ Show detailed reaction mechanisms for the following reactions, showing the structure of the expected major product. 1' NaOH/B—rz “8522 ,f \ V ‘_-_.‘\ H0 i A “P {ii/C” -———7 ‘ a a + “30 ,1 e- (3? A (1/4 0- 1L “*7 be M H 59“ ~a/4} J/ u {k «49 9c (VHg'F Cbg\ H [II . Show how you would carry out the following tranSfonnations showing the you would use in each step and the structure of the intermediate products formed. V. _ . .Rank the following compounds in decreasing order of basicity. NHz NHz NHCOCH3 OH OH é; @@ g5 N02 coon A B [c D E F J7 > A > 6 2 c > E Z r: High Basicin Scale Low VI. An unknown compound A (C 10H 120NBr) gave the pmton NMR spectrum shown below. IR Spectrum showed bands at 3450, 1725 and 1640 cm‘l. Upon heating with 6M aqueous HCl a mole of compound A gave one mole of compound B (C7H3NBr) and one mole of compound C (C3H502). Deduce the structures of compounds A, B & C. ...
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This note was uploaded on 02/15/2011 for the course CHE 118c taught by Professor Nasiri during the Spring '08 term at UC Davis.

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prac2sol - I Chem 118C / W / 09 / Nambiar/ Sample Test-2...

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