234-E2-SP08_ANS - CHEM 234 - EXAM 2 - SPRING 2008 Name: I i...

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Unformatted text preview: CHEM 234 - EXAM 2 - SPRING 2008 Name: I i E 3': Selected approximate pKa values 1. (15 points) Predict the products of the following reactions. If a reaction does not occur » Windham no reaction —— NR. A) 0“ ... 0”" CH NHCH W 3 3 98W «Ev HS he. /9 N 3 ,, (L ML , ‘87, KM ‘0 G “:32. u: r W‘ka Kc: 20 fr“ gawk 9 3;} B) o9 /\’( + /\/OH +’ NR. 0 e———-—--- ‘ -g _ a: 30‘ (“(6% 4‘ N a C _ ) 09 em: 0/ + A%“3 “ +~ /\ Mag” 2. (15 points) Draw a complete arrow-pushing mechanism for the following reaction. Include all important resonance structures for any product that is resonance~stabilized a A 0—H 3. (5 points) Name the following compound: «:1 g; r r \E if Q geufiwfi “:2 ' Kax cm: 02, gmdkj «:2 firms Jag, 4. 5 oints) Draw struc urex for the following compounds“. ( p mam (gmam 3~tert—butylcyclopentanol O A» 5. (12 points) A) Draw all of the important resonance structures for the following ion. Be sure to show arrogvg ~ 9336 pushing required to get to successive resonance structures. c EM, QC $¥m , MA : C g A M' 6" V B) Draw an orbltal overlap dragram rllustratmg the n—electron system. :5 0’ - low “#3 E2. 1 M3: m, Easerinir W "t M a 7. (16 points) A) Draw Newman projections of the MOST stable confomer and the LEAST stable conformer of the following compound. Indicate which is which, - a r c a» 4- ,-..,:~.«,.‘ Hwy”; 6'. gaywm‘u‘rxdi B) For the same structure, indicate the stereochemistry for any chiral carbon(s) as R or S. g€>m$if great g‘ Efifiwuno? -§$?Q~XAM§§#¢3§§ Me, l "’ X ~49 5 wtgmtte" é g, S. g “'“X f”? :15: c ’\ 5 geese C" figtahlwe we? o 8. (20 points) Indicate the relationship for the following pairs of structures. They may be structural (constitutional) isomers ~ SI, enantiomers - EN, or the same structure - SAME. B) C) I rig SAME: Cm / D) Br Me H Me A/ HmBr 5 I’ ...
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This note was uploaded on 09/03/2010 for the course CHEM 234 taught by Professor Bates during the Fall '08 term at University of California, Berkeley.

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234-E2-SP08_ANS - CHEM 234 - EXAM 2 - SPRING 2008 Name: I i...

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