Quiz 5 W'10 key

Quiz 5 W'10 key - * * 2 chiral centers=4 possible...

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CHEM 312 Winter ‘10 Quiz 5 Names 1. Give the IUPAC name for this compound: O OH N 4-amino-3-hydroxy-N-isopropyl-N-methylcyclohex4-enone 2. There is a nitrogen analog to the keto-enol tautomers, show below between an imine and an enamine. Calculate the H˚ for this equilibrium and determine whether the imine or the enamine form is thermodynamically favored. Is it the same or different than keto- enol tautomerization? H N N enamine imine BREAK MAKE C=N (pi) 147 C=C (pi) 270 C-H 418 N-H 448 565 kJ/mol 718 kJ/mol H˚ = -153 kJ/mol in this case, the enamine is more stable than the imine; this is the opposite result as the enol/keto equilibrium. 3. Highlight the isoprene units in cadinene, below, and star the chiral centers. How many stereoisomers are possible for this sesquiterpene?
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Unformatted text preview: * * 2 chiral centers=4 possible stereoisomers Bond Dissociation Energies ( ∆ H˚ kJ/mol) H 3 C—H 439 CH 3 CH 2 —H 418 PhCH 2 —H 368 Ph—H 464 CH 3 CH 2 —F 454 CH 3 CH 2 —Cl 335 CH 3 CH 2 —Br 284 CH 3 CH 2 —I 222 Ph—F 527 Ph—Cl 402 Ph—Br 339 Ph—I 272 H 3 C—CH 3 377 Ph—CH 3 423 PhCH 2 —CH 3 314 H 2 C=CH 2 (both) 715 H 2 C=CH 2 (pi bond) 270 H 3 C—OH 385 H 3 C—OCH 3 347 Ph—OH 464 H 2 C=O (both) 732 H 2 C=O (pi bond) 377 H 3 C—NH 2 356 Ph—NH 2 427 H 2 C=Nh (pi bond) 147 H—OH 498 H—OCH 3 435 H—O 2 CCH 3 444 H—F 569 H—Cl 431 H—Br 368 H—I 297 H—NH2 448 H—SH 381 H—H 435 F—F 159 Cl—Cl 247 Br—Br 192 I—I 151 O=O (both) 498 O=O (pi bond) 353...
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This note was uploaded on 10/24/2011 for the course CHEM 312 taught by Professor Bailey during the Spring '03 term at Cal Poly.

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Quiz 5 W'10 key - * * 2 chiral centers=4 possible...

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