1 2008 test_1a_ - 2 mark ), all curly arrows describing...

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Chemistry 2203/7 (’08) TEST 1A Name: ____________________________ Page1/1 Marks are in parentheses 1 . (6) For the molecules below, provide a systematic name ( 2 x 2 marks ) and calculate the degrees of unsaturation ( 2marks ). Indicate stereochemistry of the molecule where appropriate. H H 2a . (1) Draw the most stable conformer of ethylcyclohexane in 3D-perspective. 2b . (1) Why are alkynes easier to crystallize than cis -alkenes of equivalent carbon number? 3a . (8) Show the reagents required to execute the reactions shown below. 1. O H O H Cl 2. 1. 2. 3b . (8) Show the starting material required to yield the product shown below. Lindlar cat, H 2 OH HO H H KMnO 4 , -OH O 2 KMnO 4 , H+ 1 equiv Cl 2 hv CCl 4 (100 % yield) Chemistry 2203/7 (’07) TEST 1A Page 2/2
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3c . (8) Show the expected product(s) for each of the reactions shown below. Cl 2 , no light 1. BH 3 , 2. oxidative workup -OH H+ , H 2 O 4a . (6) MECHANISM . Draw a mechanism for the following reaction, showing all intermediate species (
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Unformatted text preview: 2 mark ), all curly arrows describing electron movement ( 3marks ) and all charges ( 1 mark ) (if applicable). H - Cl H Cl 4b . (6) Give an appropriate example to illustrate the following mechanistic concepts: syn addition anti addition Markovnikov addition 5. (6) DEDUCTION . Compound A with molecular formula C 18 H 34 O 2 is an isomer of a common fatty acid found in cell membranes. Calculate the degree of unsaturation of Compound A (the presence of oxygen does not affect this calculation): Based on this information, list the different combination of rings or multiple bonds that might be present in Compound A : When Compound A is treated with permanganate in acid (H+), a linear (nonbranched) monoacid B C 10 H 20 O 2 and a linear (non-branched) diacid C C 8 H 14 O 4 were obtained. What are the structures of A (neglect stereochemistry) , B and C ....
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1 2008 test_1a_ - 2 mark ), all curly arrows describing...

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