1-Methoxy-4-(2-methoxyethoxy)benzene, $CH X_{3} O - C X_{6} H X_{4} - O - CH X_{2} CH X_{2} - O - CH X_{3}$ (the two oxygens on the ring are para), is heated with a large excess of concentrated $HI$ . Count the moles of HI consumed per mole of the compound, assuming every alkyl carbon-oxygen bond is converted to an alkyl iodide (one HI per bond, any alcohol formed is also converted) and the aryl carbon-oxygen bonds and the phenolic OH are unchanged.

Numerical answer type, tolerance 0.5.

Answer: 4

The alkyl C-O bonds are:

CH X_{3} - O (Ar)

(1),

ArO - CH X_{2}

(1), and the two C-O bonds of the aliphatic ether

CH X_{2} - O - CH X_{3}

(2). Each converts to a C-I bond using one HI, giving 4 moles in total. The products are hydroquinone,

CH X_{3} I

(2 mol) and

ICH X_{2} CH X_{2} I