There are four isomers with the molecular formula C4H9Cl. Only one of these isomers (compound A) has a chiral center. When compound A is treated with sodium ethoxide, three products are formed: compounds B, C, and D. Compounds B and C are diastereomers, with compound B being the less stable diastereomer. Provide structures for compounds A, B, C, and D. Do you expect compound D to exhibit a signal at approximately 1650 cm−1 in its IR spectrum? Explain.

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There are four isomers with the molecular formula C4H9Cl. Only one of these isomers (compound A) has a chiral center. When compound A is treated with sodium ethoxide, three products are formed: compounds BC, and D. Compounds B and C are diastereomers, with compound B being the less stable diastereomer. Provide structures for compounds ABC, and D. Do you expect compound D to exhibit a signal at approximately 1650 cm−1 in its IR spectrum? Explain.

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