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Question 17.6.2: A compound has the molecular formula C10 H14. It gives the f......

A compound has the molecular formula C_{10}  H_{14}. It gives the following NMR data.

(i) 0.88 δ    (9 H singlet)

(ii) 7.28 δ   (5 H, singlet, aromatic protons)

Assign structure to the compounds

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(i) A nine proton singlet at 0.88 δ indicates the presence of a tertiary butyl group.

(ii) Five proton singlet at 7.28 δ confirms phenyl ring.

Hence the structural formula of the compound may be

\begin{matrix}   & &CH_3 &  & \\  & & | &  &  \\ \begin{matrix} &—— & \\ \quad \diagup \diagup &   & \diagdown \diagdown \quad \\  \diagdown & & \diagup & \\  & \overset{——}{—— }& & \end{matrix} & —& C &—&CH_3\\  & & | & & \\ & & CH_3& & \end{matrix}

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