POW-310-11-Key - nitro group at the para position Draw the...

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Last Name: UTEID: First Name: SCORE: KEY Deadline for POW 310-11: Apr 13, 2009 3:00 PM Provide the product from each sequence; draw the major isomer, except where indicated: A) B) C) D) CH 3 Br 2 NBS; CCl 4 CH 3 Br 2 FeBr 3 CH 2 Br CH 3 CH 3 Br Br 1) ClCOCH 2 CH 3 AlCl 3 2) HNO 3 ;H 2 SO 4 O NO 3 1) HNO 3 ;H 2 SO 4 2) Br 2 ; FeBr 3 Br NO 3
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p-nitrophenol and m-nitrophenol are both acidic compounds, but one isomer is more acidic than the other. Draw the various resonance structures for each anions. Predict which isomer is the more acidic and use the resonace structures to support your rationale. O NO 2 O NO 2 O NO 2 O N O O This resonance structure show the stabilizing effect of the
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Unformatted text preview: nitro group at the para position Draw the family of resonance structures to compare the relative stabilities. O N O O pKa (p-nitrophenol)= 7.2 Stronger acid than m isomer O NO 2 O O O NO 2 NO 2 NO 2 This group of resonance structures shows that the nitro group has NO stabilizing influence on the anion and therefore little effect upon the acidity. pKa (m-nitrophenol)= 8.4 Weaker acid than p isomer Draw the family of resonance structures to compare the relative stabilities....
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This note was uploaded on 03/16/2010 for the course CH 53705 taught by Professor Colapret during the Fall '09 term at University of Texas at Austin.

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POW-310-11-Key - nitro group at the para position Draw the...

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