Question

Each of the following compounds is an amine (Section 1.3B). Which line-angle formulas represent the same compound? Which represent constitutional isomers? (a) CCC(C)N (b) C1CCNC1 (c) CCNCC (d) CC(C)CN (e) CCCNC (f) CCCCN (g) CCC(C)N (h) C1CCNCC1

Short answer

Answer: Compounds a and g are the same compound, and the rest (b, c, d, e, f, and h) are constitutional isomers.

Step-by-step solution

Convert SMILES notation into structural formulas

For each compound, we need to convert the given SMILES notation into a structural formula. (a) CCC(C)N = CH3CH2CH(CH3)NH2 (b) C1CCNC1 = Cyclic structure with four carbons and one nitrogen in the ring (c) CCNCC = CH3CH2NHCH2CH3 (d) CC(C)CN = CH3C(CH3)NHCH3 (e) CCCNC = CH3CH2CH2NCH3 (f) CCCCN = CH3CH2CH2CH2NH2 (g) CCC(C)N = CH3CH2CH(CH3)NH2 (same as compound a) (h) C1CCNCC1 = Cyclic structure with five carbons and one nitrogen in the ring

Compare structural formulas and determine the same compound or constitutional isomers

Now that we have the structural formulas, we can compare them to determine which compounds are the same or constitutional isomers. - Compounds a and g are the same as they have the same structural formula, CH3CH2CH(CH3)NH2. - Compound b is a constitutional isomer of compounds c, d, and e since they all have the same molecular formula (C4H11N) but different connectivity. - Compounds c and e are also constitutional isomers as they have the same molecular formula (C4H11N) but different connectivity. - Compounds d and f are constitutional isomers. They share the same molecular formula (C4H11N) but have different connectivity. - Compound h is a constitutional isomer of compounds b, c, d, e, and f since they all have the same molecular formula (C4H11N) but different connectivity. In summary, compounds a and g are the same compound, and the rest are constitutional isomers.