Question

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? Which represent constitutional isomers? (a) CCC(C)O (c) OCC1CC1 (d) CC(C)CO (e) CC(C)CO (f) CCCCO (g) CCC(C)O (h) CC1(O)CCCCC1

Short answer

Answer: (a) and (g) represent the same compound. (d) and (e) represent the same compound. The pairs of constitutional isomers are: (a) (or (g)) with (d) (or (e)), (a) (or (g)) with (f), and (d) (or (e)) with (f).

Step-by-step solution

Convert SMILES to Molecular Formulas

First, let's write down the molecular formulas for each compound based on their SMILES notations: (a) CCC(C)O = C4H10O (c) OCC1CC1 = C4H8O (d) CC(C)CO = C4H10O (e) CC(C)CO = C4H10O (f) CCCCCO = C5H12O (g) CCC(C)O = C4H10O (h) CC1(O)CCCCC1 = C6H12O

Identify Same Compounds

Compare the SMILES notations to see which structures represent the same compounds: (a) and (g) both have the same SMILES (CCC(C)O) and represent the same compound. (d) and (e) both have the same SMILES (CC(C)CO) and represent the same compound.

Identify Constitutional Isomers

Compare the molecular formulas to identify constitutional isomers: (a) (or (g)), (d) (or (e)), and (f) all have the molecular formula C4H10O but different SMILES notations. Therefore, they are constitutional isomers. (c) and (h) have different molecular formulas from the rest and are not related as constitutional isomers. So, the pairs of constitutional isomers are: - (a) (or (g)) with (d) (or (e)) - (a) (or (g)) with (f) - (d) (or (e)) with (f)