Excess $LiAlH X_{4}$ is used, followed by aqueous work-up, on the compound shown. Count one hydride ion ( $H X^{-}$ ) for each ketone or aldehyde group, two for each ester and two for each nitrile (hydride delivered to carbon only; hydrogens from work-up are not counted). How many moles of hydride ion are consumed per mole of the compound? Give the answer as an integer.

Numerical answer type, tolerance 0.5.

Answer: 5

The compound has one ketone (1

H X^{-}

), one ester (2

H X^{-}

) and one nitrile (2

H X^{-}

). Total

= 1 + 2 + 2 = 5

. The products after work-up are an amino diol bearing a primary amine, a secondary alcohol and a primary alcohol (plus methanol).