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2007_test_2C_answers - TEST 2C Page 2/2 3c(8 Show the...

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Chemistry 2203/7 (’07) TEST 2C Name: Abenor’s Answer 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 ) and assign the absolute configuration to the molecule on the left ( 1 mark ) R ; What is the degree of unsaturation of the molecule on the right ? One 3-ethyl-6-hepten-4-ol Cl F F Cl OH 1,2-dichloro-3,4- difluorocyclobutane 2a . (1) Why is t-butanol totally soluble in water but not n-butanol? Approximately spherical shape fits well into H-bonding network of water 2b . (1) Why do chlorine atoms hydrogen bond less efficiently than fluorine atoms ? Cl less electronegative than fluorine, size mismatch between Cl and H 3a . (8) Show the reagents required to execute the reactions shown below. Br CF 3 CF 2 I Br OTs SH HCF 2 CF 3 -SH LiAlH 4 -C= CH -OtBu 3b . (8) Show the starting material required to give the product(s) shown below. LiAlH 4 HBr -CN OH HO O O Br CN CrO 3 , H+ Br OH HO Br HO
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Chemistry 2203/7 (’07)
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Unformatted text preview: TEST 2C Page 2/2 3c . (8) Show the expected product (s) if any , for each of the reactions shown below. OH OTs F-Cl-OH E2 conditions Br OH TsCl No reaction Cl OTs 4a . (6) MECHANISM. Draw a mechanism for the following reaction, showing all intermediates ( 1 mark ), all curly arrows describing electron movement ( 4 marks ) and all charges ( 1 mark ) (if applicable). OH, E2conditions I H I H OH-4b .(6) Use the appropriate chemical equations to show why ethoxide (EtOH, pKa 17) is capable of quantitatively deprotonating HCN (HCN pKa 9). ETOH + H2O ← → ETO- + H3O + Ka 10 -17 Rxn 1 HCN + H2O ← →-CN + H3O + Ka 10 -9 Rxn 2 Add Rxn 1-1 + Rxn 2 HCN + EtO- ← →-CN + EtOH K 10 8 favourable!! 5. (6) Stereochemistry . Draw all structural isomers of C 4 H 10 O and indicate which isomers are chiral if any. Include ethers (ROR) and alcohols (ROH). OH OH OH O OH O O chiral...
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2007_test_2C_answers - TEST 2C Page 2/2 3c(8 Show the...

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