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CHE201 - Exam 2 2007 Answer

CHE201 - Exam 2 2007 Answer - Organic Chemistry 2011203...

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Organic Chemistry 2011203 Midterm 2 November 2,2007 I 1:00-1 1:50 am h"rrLru( W Name (Print) Signature Student ID number Problem I (30 pts) Score II (30 pts) m (30pts) IV (30 pts) (30 pts) Total (150 pts)
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PROBLEM I Draw one example of each of the following (5 pts each) (1) A secondary carbocation (2) A tr ans-cycloalkene (3) A bicyclic alkene with an internal mirror plane (4) A strong nucleophile (5) A strong base but weak nucleophile w uR @peu, {At "^1J / 1trX-O{"^, \ cu 11? (6) A secondary halide ry U-
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PROBLEM II (1) Draw and name uff6il.iir\rhich have the molecular formula C+Hs. (15 pts) Hint: include geometric isomers. C'Y\ y ilS: cn- cH; q\{3 Ct{ " C:C- v1 C-{^t r'\ C ,/ Fl c41 ? \1 \ L\ :(A \' Q'l; ar c, - vl i cKr ,z cfi; q{ ) (}I 4 \. ,i( ,1rr\ (3) If (S)-glyceraldehyde has a specific rotation of -8.7o, what is the specific rotation of (R)- glyceraldehyde? (5 pts) A %t (2) Draw the structure of (S)-3-chloro-3-methylhexane. Take particular care to indicate stereochemistry properly. (1 0 pts) r 8.+
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PROBLEM III (1) Consider the following molecule: H 9Ht oe U17 o-+ n+ *,-1-- - | .* c,{.L I j I I I I :cl n --t7 l\* :H cl H (a) How many chiral
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