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Question
What is the relationship between the members of following pairs of structures? Are they structural or geometrical isomers or resonance contributors?
\[\begin{array}{cc}\ce{^+OH}\\||\\
\ce{H - C - OH}\end{array}\]
\[\begin{array}{cc}\ce{OH}\phantom{.}\\|\phantom{...}\\
\ce{H - C^+ - OH}\end{array}\]
Solution
The given structures are canonical structures or contributing structures. They are hypothetical and individually do not represent any real molecule. Hence, the given pair represents resonance structures, called resonance isomers.
\[\begin{array}{cc}\ce{^+OH}\\||\\
\ce{H - C - OH}\end{array}\]
\[\begin{array}{cc}\ce{OH}\phantom{.}\\|\phantom{...}\\
\ce{H - C^+ - OH}\end{array}\]
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\[\begin{array}{cc}
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| I. | \[\begin{array}{cc} \phantom{.......................}\ce{O}\\ \phantom{.......................}||\\ \ce{CH3 - CH2 - CH2 - CH2 - C - H} \end{array}\] |
| II. | \[\begin{array}{cc} \phantom{.................}\ce{O}\\ \phantom{.................}||\\ \ce{CH3 - CH2 - CH2 - C - H} \end{array}\] |
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| IV. | \[\begin{array}{cc} \ce{CH3 - CH - CH2 - C - H}\\ \phantom{...}|\phantom{............}||\phantom{}\\ \phantom{...}\ce{CH3}\phantom{.........}\ce{O}\phantom{} \end{array}\] |
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| I. | \[\begin{array}{cc} \phantom{.......................}\ce{O}\\ \phantom{.......................}||\\ \ce{CH3 - CH2 - CH2 - CH2 - C - H} \end{array}\] |
| II. | \[\begin{array}{cc} \phantom{.................}\ce{O}\\ \phantom{.................}||\\ \ce{CH3 - CH2 - CH2 - C - H} \end{array}\] |
| III. | \[\begin{array}{cc} \ce{CH3 - CH2 - C - CH2 - CH3}\\ \phantom{}||\\ \phantom{}\ce{O} \end{array}\] |
| IV. | \[\begin{array}{cc} \ce{CH3 - CH - CH2 - C - H}\\ \phantom{...}|\phantom{............}||\phantom{}\\ \phantom{...}\ce{CH3}\phantom{.........}\ce{O}\phantom{} \end{array}\] |
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