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Chapter 2: Problem 21

Each member of the following set of compounds is an alcohol; that is, each contains an -OH (hydroxyl group, Section 1.3A). Which structural formulas represent the same compound, and which represent constitutional isomers? (a) CCC(C)O (b) OC1CCC1 (c) OCC1CC1 (d) CC(C)CO (e) CC(C)CO (f) CCCCO \((\mathrm{g})\) CCC(C)O (h) CC1(O)CCCCC1

Short Answer

Expert verified
Answer: Compounds (a), (d), (e), and (g) represent the same compound, 2-Butanol. Compounds (b) and (c) are constitutional isomers, with (b) being Cyclopropylmethanol and (c) being Ethylcyclopropane. Compound (f), 1-Butanol, is a structural isomer of 2-Butanol. Compound (h), Cyclohexanol, is unique and not a constitutional isomer of any other compound given.

Step by step solution

01

Convert SMILES notation to compound structures

First, we will convert each SMILES notation into a structure. (a) CCC(C)O --> 2-Butanol (b) OC1CCC1 --> Cyclopropylmethanol (c) OCC1CC1 --> Ethylcyclopropane (d) CC(C)CO --> 2-Butanol (e) CC(C)CO --> 2-Butanol (f) CCCCO --> 1-Butanol (g) CCC(C)O --> 2-Butanol (h) CC1(O)CCCCC1 --> Cyclohexanol
02

Compare the compound structures

Now, we will compare the structures of each alcohol to determine which are the same and which are constitutional isomers. (a) and (d) and (e) and (g) represent the same compound 2-Butanol. (b) and (c) are constitutional isomers, as they have the same molecular formula (C4H8O) but different connectivities. (b) is Cyclopropylmethanol, and (c) is Ethylcyclopropane. (f) 1-Butanol is a structural isomer of (a), (d), (e), and (g) 2-Butanol as it has the same molecular formula (C4H10O) but different connectivities. (h) Cyclohexanol is not the same as any other compounds, and it is not a constitutional isomer of any other compound given.

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Most popular questions from this chapter

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