Problems and exercisesAromaticity

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1. Aromatic, nonaromatic or antiaromatic

Indicate whether each of the following compounds is aromatic, nonaromatic or antiaromatic.

Six compounds: a) cyclooctatetraene; b) cyclopentadienyl cation; c) cyclopentadienyl anion; d) [10]-annulene; e) azulene; f) [18]-annulene

2. Lone pairs and aromaticity

For the following compounds, determine which lone pairs are involved in aromaticity.

Eight compounds: a) furan; b) 1H-azepine; c) thiazole; d) pyrylium cation; e) 1,4-dioxin; f) caffeine; g) moxonidine; h) a pyrido[1,2-a]pyrimidinone derivative bearing a tetrazole

3. Hückel rule

How many π electrons do the cyclopropenyl cation, the cyclopropenyl anion and the cycloheptatrienyl (tropylium) cation have? Which of them are aromatic?

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