Week_4.2_PurpleBook_Answers

Week_4.2_PurpleBook_Answers - 97 Conjugation and Resonance...

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H 2 CC CH 2 H 2 C H C H CH 2 H 2 H C H C C H C H 2 NH Conjugation and Resonance 1. For each of the following species, if there is a conjugated π -system, circle all the atoms which are involved in that conjugated system. they're orthogonal! Week 4 97
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N N H 3 C CH 3 O 2 N COOH NO 2 HOOC H H 3 C H CH 3 NH 2 H H H 2 N CC C H 3 H H 3 C CH 3 CH 3 C H CH 3 H H 3 C H H 3 C H CH 3 NH 2 H H H 2 N Allenes and Other Unusual Types of Chirality 1. Each of the following molecules is chiral. Can you explain the origin of asymmetry in each molecule? Modify each molecule so that it is no longer chiral. Classic allene chirality: the end groups are in orthogonal planes: Molecule will be achiral if, for instance, 3 groups are replaced with H's. Very similar to allene chirality: Note that there is a stereogenic carbon! Why are the four substituents different? Again, similar to allene chirality. Consider the "spiro" ring fusion: Molecule will be achiral if, for instance, 3 groups are replaced with H's. O 2 N COOH NO 2 HOOC Why should we argue that the terminal carbon atoms are stereogenic carbons? Molecule will be achiral if, for instance, NH 2 groups are replaced with H's.
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This note was uploaded on 05/01/2008 for the course CHEM 51 taught by Professor Gribble during the Spring '08 term at Dartmouth.

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Week_4.2_PurpleBook_Answers - 97 Conjugation and Resonance...

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