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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?
Solution
Compounds having the same molecular formula but with different structures are called structural isomers. The given compounds have the same molecular formula but they differ in the position of the functional group (ketone group).
In structure I, ketone group is at the C-3 of the parent chain (hexane chain) and in structure II, ketone group is at the C-2 of the parent chain (hexane chain). Hence, the given pair represents structural isomers.
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\[\begin{array}{cc}
\ce{D}\phantom{......}\ce{H}\\
\backslash\phantom{......}/\\
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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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| 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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| I. | CH3 – CH2 – CH2 – CH2 – OH |
| II. | \[\begin{array}{cc} \ce{CH3 - CH2 - CH - CH3}\\ \phantom{.....}|\\ \phantom{.......}\ce{OH} \end{array}\] |
| III. | \[\begin{array}{cc} \phantom{...}\ce{CH3}\\ \phantom{}|\\ \ce{CH3 - C - CH3}\\ \phantom{}|\\ \phantom{..}\ce{OH} \end{array}\] |
| IV. | \[\begin{array}{cc} \ce{CH3 - CH - CH2 - OH}\\ |\phantom{........}\\ \ce{CH3}\phantom{......} \end{array}\] |
| V. | CH3 – CH2 – O – CH2 – CH3 |
| VI. | CH3 – O – CH2 – CH2 – CH3 |
| VII. | \[\begin{array}{cc} \ce{CH3 - O - CH - CH3}\\ \phantom{...}|\\ \phantom{......}\ce{CH3} \end{array}\] |
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| I. | CH3 – CH2 – CH2 – CH2 – OH |
| II. | \[\begin{array}{cc} \ce{CH3 - CH2 - CH - CH3}\\ \phantom{.....}|\\ \phantom{.......}\ce{OH} \end{array}\] |
| III. | \[\begin{array}{cc} \phantom{...}\ce{CH3}\\ \phantom{}|\\ \ce{CH3 - C - CH3}\\ \phantom{}|\\ \phantom{..}\ce{OH} \end{array}\] |
| IV. | \[\begin{array}{cc} \ce{CH3 - CH - CH2 - OH}\\ |\phantom{........}\\ \ce{CH3}\phantom{......} \end{array}\] |
| V. | CH3 – CH2 – O – CH2 – CH3 |
| VI. | CH3 – O – CH2 – CH2 – CH3 |
| VII. | \[\begin{array}{cc} \ce{CH3 - O - CH - CH3}\\ \phantom{...}|\\ \phantom{......}\ce{CH3} \end{array}\] |
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| I. | CH3 – CH2 – CH2 – CH2 – OH |
| II. | \[\begin{array}{cc} \ce{CH3 - CH2 - CH - CH3}\\ \phantom{.....}|\\ \phantom{.......}\ce{OH} \end{array}\] |
| III. | \[\begin{array}{cc} \phantom{...}\ce{CH3}\\ \phantom{}|\\ \ce{CH3 - C - CH3}\\ \phantom{}|\\ \phantom{..}\ce{OH} \end{array}\] |
| IV. | \[\begin{array}{cc} \ce{CH3 - CH - CH2 - OH}\\ |\phantom{........}\\ \ce{CH3}\phantom{......} \end{array}\] |
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| VII. | \[\begin{array}{cc} \ce{CH3 - O - CH - CH3}\\ \phantom{...}|\\ \phantom{......}\ce{CH3} \end{array}\] |
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