Deuterium is an isotope of hydrogen specified the symbol D and it not detectable by HNMR spectroscopy. As preparing for an electrophilic aromatic substitution lab, chemist mistakenly mixes an aqueous solution of DCL with 78 grams of benzene. He place the mixture in a separator funnel adds pentane, drains out the bottom layer as well as collects the top layer. He then places the top layer on the rotary evaporator to remove any pentane as well as discovers he now has 84 grams of material. While he checks the HNMR spectra of this material he observes no signals- what happened?