circle the molecules below which you would expect to be extra stable, and draw a box around any molecules which you would expect to be particularly unstable. Assume molecules are planar, and do not focus on angle strain issues (that is, are the first two molecules more or less stable than other 3-membered rings with one C=C double bond?). NH

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Chapter1: Chemical Foundations
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circle the molecules below which you would expect to be extra
stable, and draw a box around any molecules which you would expect to be particularly
unstable. Assume molecules are planar, and do not focus on angle strain issues (that is, are the
first two molecules more or less stable than other 3-membered rings with one C=C double
bond?).
NH
NH
The last molecule has an IR spectrum which does not match the structure drawn.
Specifically, it does not possess a strong carbonyl absorption anywhere near 1700 cm-. What
does this tell you about the actual structure of the molecule? Draw the mechanism for a reaction,
catalyzed by basic water, by which it forms a constitutional isomer, and explain why this
isomerization reaction is both rapid and exothermic.
H
НО
H,O
Do you expect a similar rapid, exothermic isomerization for the second-to-last molecule (the
4-membered amide)? Why or why not? Draw the structure of the analogous isomer.
Transcribed Image Text:circle the molecules below which you would expect to be extra stable, and draw a box around any molecules which you would expect to be particularly unstable. Assume molecules are planar, and do not focus on angle strain issues (that is, are the first two molecules more or less stable than other 3-membered rings with one C=C double bond?). NH NH The last molecule has an IR spectrum which does not match the structure drawn. Specifically, it does not possess a strong carbonyl absorption anywhere near 1700 cm-. What does this tell you about the actual structure of the molecule? Draw the mechanism for a reaction, catalyzed by basic water, by which it forms a constitutional isomer, and explain why this isomerization reaction is both rapid and exothermic. H НО H,O Do you expect a similar rapid, exothermic isomerization for the second-to-last molecule (the 4-membered amide)? Why or why not? Draw the structure of the analogous isomer.
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