If the SN2 reaction of an aromatic alcohol with an alkyl halide, like the synthesis of nerolin, is successful, what changes would be seen in the IR spectrum for the product compared to the starting material

O-H stretch signal at 3300 cm-1

Explanation:

In this question, we can start with the reaction mechanism for the synthesis of Nerolin. We have to start with naphthalen-2-ol adding NaOH we can produce the alkoxide. Then this alkoxide can react by an Sn2 reaction with bromomethane to produce Nerolin (see figure 1).

In the starting molecule (naphthalen-2-ol) we have an "OH" group. Therefore we will have an O-H stretch signal around 3300 cm^-1. The alcohol signals are very broad and very intense, so this will be the main signal for the initial molecule. In the final product, we dont have the "OH" therefore this signal will disappear (see figure 2).

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