058-RG1-ProbSol-10 - Why do you suppose that arylamines,...

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Chem 1058 Handout #3 J. Walcott LEARNING STRATEGIES CENTER Spring 2010 Review Guide #1 Supplemental Problems Solutions 1. Please check answers in the Solutions Manual. 2. There are five resonance structures for Phenanthrene. Which carbon-carbon bond is the shortest? The circled bond represents a double bond in four of the five resonance forms. This bond has more double-bond character and thus is shorter than the other carbon-carbon bonds of Phenanthrene. (from McMurry, Organic Chemistry ) 3. There are also five resonance structures for Analine (one is shown). Draw the other four.
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Unformatted text preview: Why do you suppose that arylamines, such as Analine, are weaker bases than alkylamines? NH 2 Chem 1058 CENTER FOR LEARNING AND TEACHING Handout #3 Page 2 LEARNING STRATEGIES CENTER Spring 2010 3. Arylamines, such as Aniline, are weaker bases than alkylamines because the nitrogen lone-pair electrons of arylamines are delocalized by interactions with the aromatic ring electron system and are less available for bonding to H + . Analine is stabilized because of the five resonance structures. (from McMurry, Organic Chemistry ) NH 2 NH 2 NH 2 NH 2 NH 2...
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058-RG1-ProbSol-10 - Why do you suppose that arylamines,...

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