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Sasakiexam2 - CHEM 239U Spring 2005 Prof Sasaki EXAM#2 Name...

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CHEM 239U Spring, 2005 EXAM #2 Name . Prof. Sasaki 150 points TOTAL Good Luck! Note: Only answers in the box will be graded. ________________________________________________________________________ 1. (35) (a) Rank the amines in each set in order of increasing basicity (indicate “1” for the most basic amine, and “3” for the least basic amine). (i) NH 2 NH 2 NH 2 NC H 3 C (ii) NH 2 NH 2 H N (iii) NH N NH (b) Consider the following compounds. (i) N-Ethyl-N-methylaniline (ii) 1-Methylbutylamine (iii) (iv) N H 3 C CH 2 CH 3 Cl N H 3 C CH 2 CH 3 Cl (b-1) Write the structure of compounds (i) and (ii). (b-2) Which compound(s) are capable of being resolved into enantiomers at room temperature?
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CHEM 239U page 2 Name . 2. (40) (a) Give the structure of the Claisen condensation product of ethyl phenylacetate (C 6 H 5 CH 2 COOCH 2 CH 3 ) (b) What ketone would you isolate after saponification and decarboxylation of this Claisen condensation product? (c) What ketone would you isolate after treatment of the Claisen condensation product of ethyl phenylacetate with sodium ethoxide and allyl bromide (CH 2 =CHCH 2 Br), followed by saponification and decarboxylation?
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