14C_s11_lec02_finalB

14C_s11_lec02_finalB - Chemistry 14C Lecture 2 Spring 2011...

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Chemistry 14C Lecture 2 Spring 2011 Final Exam Part B Page 1 Page 1 score = The questions on page one and two of exam part B refer to the following reaction sequence, a small portion of the work your instructor did many years ago. C A LiOH CH 3 OH O OH C O O - Li + B C Li + - O O - Li + 1) CH 3 I 2) CH 2 N 2 C C H 3 C O OCH 3 PDC (CH 3 ) 3 COOH D C H 3 C O OCH 3 O h ν CH 3 O CN E F h ν OH C CH 3 G CF 3 CO 2 H OH C CH 3 H Birch reduction N N N N N N N O OCH 3 O OCH 3 O OCH 3 1. (2) Which molecule has the greatest number of sp 3 atoms? Circle one: A B C D E F G H 2. (2) Write a number in the blank. Molecule E has ___________ lone pairs. 3. (4) Write the names of all functional groups in molecule E . Questions 4 and 5 concern the resonance of molecule C . C O O N Molecule C contributor I Contributor J 4. (3) Draw in the Contributor J box another significant resonance contributor for molecule C . Less significant contributors will earn less significant credit . Include all formal charges and lone pairs. 5. (4) Circle ' I ' or ' J ' as appropriate, then complete this sentence by adding no more than fifteen words . Between contributors I and J , contributor I / J is the less significant contributor because... 6. (4) Complete this statement by writing a number in each blank. Molecule E has ___________ conjugated atoms. In molecule E the greatest number of atoms that always lie in the same plane is ___________.
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Chemistry 14C Lecture 2 Spring 2011 Final Exam Part B Page 2
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