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mt no2 answers - Chem 140C Midterm I January 26, 2009 Q1_(7...

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Chem 140C Midterm I January 26, 2009 Q1_________(7 points) Q2_________(8 points) Q3_________(15 points) Q4_________(15 points) Q5_________(20 points) Q6_________(20 points) Q7_________(15 points) Total_________(100 points) Only use the front side of each page for your answers. Nothing on the back sides will be graded. If you write the exam in pencil or erasable pen, you give up your right to any kind of regrade. Name_______________________ PID#_________________________
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1. Resonance and Inductive Effects (7 points). Place the compounds below in order of increasing reactivity with nucleophiles in a nucleophilic addition process. Clearly explain the rationale for your choice. The amide will be less reactive than any of the esters due to greater resonance interaction of the carbonyl with the nitrogen atom vs. the ester oxygen. The ester (2) is next because it has the most electron rich carbonyl of all the esters because there is not an inductive electron withdrawing halogen in the molecule.
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This note was uploaded on 09/02/2009 for the course CHEM 140C taught by Professor Nefzi during the Spring '06 term at UCSD.

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mt no2 answers - Chem 140C Midterm I January 26, 2009 Q1_(7...

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