Solutions_Manual_for_Organic_Chemistry_6th_Ed 364

Solutions_Manual_for_Organic_Chemistry_6th_Ed 364 - 1 6-42...

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Unformatted text preview: 1 6-42 (a) �H l:J" H �C-- H 0 .. aromatic ( c) V- Cl ""-H Ag+ r>-- + � CH H (d) a romatic �::: C N aOH . r:} O CH aromatic -H a romatic H (e) C4 H9Li .. 1 6-43 These four bases can be aromatic, partially aromatic, or aromatic in a tautomeric form. In other words, aromaticity plays an i mportant role in the chemistry of all four structures. (Only electron pairs involved in the important resonance are shown . ) For part (b) , nitrogens that are basic are denoted by B. T hose that are not basic are shown as NB. Note that some nitrogens change depending on the tautomeric form. (a) and (c) O C 1- (f) comatk Y Cl 0 A g+ .. ()-o •• •• o 0 + H aromatic cytosine aromatic to the extent that this resonance form contributes aromatic {� � NB I :0: N H � BH / O. •• • • uracil a romatic to the extent that this resonance form contributes 358 r�.:_ l_ 7� . :0: + .. N H I NB O· • •• r� � N OH B BN OH t automer­ aromatic continued on the next page ...
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This note was uploaded on 02/27/2010 for the course CHEM 140 taught by Professor Wade during the Spring '10 term at Whitman.

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