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HW17 - You should be able to draw 5 resonance structures...

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CH 310N Spring 2008 Last Name: First Name: Dr. Bocknack UTEID: Score: Graded Homework Problem #17 Deadline : 3:00 p.m., Monday, 4/14/08 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. 1,3-Cyclopentadiene has a pK a of 16. 1,3,5- Cycloheptatriene has a pK a of 39. The most acidic proton in each of these compounds is circled in the structures given below: H H 1,3-Cyclopentadiene pKa = 16 H H 1,3,5-Cycloheptatriene pKa = 39 H H H H H H H H H H (a) (5 points) Draw all important contributing resonance structures for the conjugate base of 1,3- cyclopentadiene.
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Unformatted text preview: You should be able to draw 5 resonance structures for this anion. (b) (7 points) Draw all important contributing resonance structures for the conjugate base of 1,3,5-cycloheptatriene. You should be able to draw 7 resonance structures for this anion. (c) (8 points) Why is 1,3,5-cycloheptatriene a weaker acid than 1,3-cyclopentadiene, even though its conjugate base has more contributing resonance structures? Use the back of this page if you need more space for your answer. (Hint : Think about the concept of aromaticity…)...
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