Consider the highly stable tert-butyl free radical intermediate (). What is the absolute total numbe — GOC and Organic Chemistry Basics Chemistry Question
Question
Consider the highly stable tert-butyl free radical intermediate ($(CH_3)_3C^\bullet$). What is the absolute total number of adjacent C-H $\sigma$ -bonds that are capable of parallel overlap with the half-filled p-orbital to stabilize the radical center?
Answer: 9
💡 Solution & Explanation
The central $sp^2$ hybridized carbon atom, which bears the unpaired odd electron in a p-orbital, is flanked directly by three separate methyl ($-CH_3$) groups. Each methyl group contains 3 $\alpha$ -C-H $\sigma$ -bonds. Therefore, there are exactly $3 \times 3 = 9$ bonds available for hyperconjugative stabilization.
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