2007_test_2D_answers - product (s) if any , for each of the...

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Chemistry 2203/7 (’07) TEST 2D Name: ____________________________ Page1/1 Marks are in parentheses Marked tests can be picked up THIS FRIDAY 11:30 AM in AT 301! 1 . (6) For the molecules below, provide a systematic name ( 2 x 2 marks ). Assign the absolute configuration to the molecule on the left ( 1 mark ). ( R ) Calculate the degree of unsaturation of the molecule on the right? Zero 5-heptyn-2-ol OH Cl F F 3-chloro-2,3-difluoropentane 2a . (1) Draw the hydrogen bonding interactions of an alcohol to water . H …OH 2 HO-H…. . O-R 2b . (1) A 1 litre bottle of CCl 4 weighs significantly more than a 1 litre bottle of CH 3 OH? Why? Density of CCl4 is so much greater than that of methanol 3a . (8) Show the reagents required to execute the reactions shown below. CH 3 CH 2 Br OTs Cl- LiAlH4 Br OH OH CrO3 NaH Cl CH 3 CH 3 OH O O 3b . (8) Show the starting material required to give the product(s) shown below. NC CN -OtBu LiAlH 4 PBr 3 HO HO O NH 2 H 2 N Br CrO 3 , H+ Br
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Chemistry 2203/7 (’07) TEST 2D Page 2/2 3c . (8) Show the expected
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Unformatted text preview: product (s) if any , for each of the reactions shown below. OTs OH F-- SCH 3 Br OH TsCl OH, SN 1 conditions SCH 3 OTs HO No rxn 4a . (6) MECHANISM. Draw a mechanism for the following reaction, showing the intermediate ( 2 marks ), all curly arrows describing electron movement ( 2 marks ) and all charges ( 1 mark ) (if applicable). Does this reaction go with inversion or racemization? ( 1 mark ) racemization OH, S N 1 conditions Cl HO + HO H-OH 4b .(6) Use the appropriate chemical equations to show why NaNH 2 (NH 3 , pKa 33) is capable of quantitatively deprotonating an alcohol (ROH pKa 16). NH3 + H2O NH2- + H3O + Ka 10 -33 Rxn 1 HOR + H2O -OR + H3O + Ka 10 -17 Rxn 2 Add Rxn 1-1 + Rxn 2 HOR + NH2- -OR + NH3 K 10 16 favourable!! 5. (6) Stereochemistry . Draw all of the structural isomers of C 4 H 9 Cl and indicate which of the molecules, if any is chiral. Cl Cl Cl Cl chiral...
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This note was uploaded on 07/28/2009 for the course CHEMISTRY CHEM 2203 taught by Professor Levin during the Spring '08 term at Indian Institute of Technology, Chennai.

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2007_test_2D_answers - product (s) if any , for each of the...

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