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. (Hint: See Section 9.15.)

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Examine the 1H NMR spectrum: Identify the number of distinct signals and their integration values, which correspond to the number of protons.

Analyze the signal at around 0.9 ppm with an integration of 9H, suggesting a tert-butyl group (C(CH3)3).

Look at the signal at around 1.2 ppm with an integration of 6H, indicating two equivalent methyl groups, likely from an ethyl group (CH3CH2-).

Consider the signal at around 3.5 ppm with an integration of 2H, which is typical for methylene protons adjacent to an electronegative atom, such as in an ethoxy group (CH3CH2O-).

Identify the signal at around 1.5 ppm with an integration of 1H, which could be a proton on a carbon adjacent to the alkoxide oxygen, suggesting the presence of an isopropoxide ion (CH3)2CHO-.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Alkyl Halides

Alkyl halides are organic compounds containing a carbon atom bonded to a halogen atom (F, Cl, Br, or I). They are important in organic synthesis and can undergo various reactions, including nucleophilic substitution. Understanding the structure and reactivity of alkyl halides is crucial for predicting the products of reactions involving these compounds.

Alkoxide Ions

Alkoxide ions are negatively charged species formed by deprotonation of alcohols. They are strong nucleophiles and are commonly used in organic reactions, such as the formation of ethers or in nucleophilic substitution reactions with alkyl halides. Recognizing the structure and reactivity of alkoxides is essential for understanding their role in organic synthesis.

1H NMR Spectroscopy

1H NMR (proton nuclear magnetic resonance) spectroscopy is a powerful analytical technique used to determine the structure of organic compounds. It provides information about the number of hydrogen atoms in different environments, allowing chemists to deduce molecular structure. Peaks in the NMR spectrum correspond to different hydrogen environments, and their integration reveals the relative number of protons, which is key to identifying the alkyl halide and alkoxide in the reaction.