Question

An alkyl halide reacts with an alkoxide ion to form a compound whose ¹H NMR spectrum is shown here. Identify the alkyl halide and the alkoxide ion.

Short answer

The given ¹H NMR spectrum represents the compound tert-butyl methyl ether. So, according to Williamson ether synthesis, following are the structures of alkyl halide and alkoxide ion.

Step-by-step solution

Step-by-step Solution Step 1: Identification of the compound

The given ¹H NMR spectrum represents the compound tert-butyl methyl ether.

The Williamson Ether Synthesis

Williamson Ether Synthesis is the reaction that uses deprotonated alcohol and an organohalide to form ether.The most useful method of preparing ethers involves Williamson ethersynthesis,in which an alkoxide ion reacts with a primary alkyl halide or tosylatein an S_N2 reaction. The structure of ethers was proved due to this chemical reaction. The alkoxide ion is normally prepared by reaction of an alcohol with a strong base such as sodium hydride, NaH. For example, ethers are synthesized by the reaction of an alkyl halide with an alkoxide ion. This reaction is called the Williamson ether synthesis.

Identify the alkyl halide and the alkoxide ion

As we know that ethers are synthesized by the reaction of an alkyl halide with an alkoxide ion, this reaction is called the Williamson ether synthesis. We have the structure of ether i.e., the product of the Williamson reaction, through which we can predict the reactants structure.

Thus, the given compound has methyl bromide as an alkyl halide and 2-methyl-propane-2-olate as an alkoxide ion which reacts to give tert-butyl methyl ether as shown in the above reaction.