Chapter 19, Problem 62P

(a) Deduce the structure of product A, which is highly symmetrical:

The following are selected spectral data for A:

MS $\left(\text{m/z}\right):220\left(M{\cdot }^{+}\right)$

IR $\left(c{m}^{-1}\right)$: 2930, 2860, 1715

${}^{1}H$ NMR $\left(\delta \right)$: 1.25 (m), 1.29 (m), 1.76 (m), 1.77 (m), 2.14 (s), and 2.22 (t); (area ratios 2:1:2:1:2:2, respectively)

$\begin{array}{l}{}^{13}CNMR\left(\delta \right):23\left(C{H}_2\right),26\left(C{H}_2\right),27\left(C{H}_2\right),29\left(C\right),39\left(CH\right),41\left(C{H}_2\right),46\left(C{H}_2\right),\\ 208\left(C\right)\end{array}$

(b) Write a mechanism that explains the formation of A.