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Question: 4. This problem will help you more clearly understand the relationship between stereochemistry an…

by | Nov 28, 2023 | questions



Question: 4. This problem will help you more clearly understand the relationship between stereochemistry an...

Show transcribed image text 4. This problem will help you more clearly understand the relationship between stereochemistry and organic reactions. In the course of a synthesis, a chemist attempted the following Sw2 reaction on a structurally complex substrate: KCN (expected) The next step in the sequence was a nitile reduction, a reaction you learned in lecture 5 that converts the -CN of a nitrile into a primary amine, -CH2NH2, as shown below: CN NH2 . LiAIH4. Et O 2. NH4CI (expected) (nitrile reduction) (expected) However, distinct amine products formed, which implies (since the nitrile reduction above does not affect stereochemistry) that there were actually two nitrile products formed from the very first substitution reaction! The chemist immediately suspected that the substitution did not proceed with complete inversion as expected. when the chemist analyzed the product, it was found that there were actually two a. Assuming that the chemist is correct and the substitution did not proceed with complete inversion, draw the two products that would result from the reaction above. b. What is the specific relationship between the products in part (a), and how might this help the chemist understand how to separate them? c. Provide a brief explanation for why the original substitution reaction did not proceed exclusively with inversion of stereochemistry as expected.

4. This problem will help you more clearly understand the relationship between stereochemistry and organic reactions. In the course of a synthesis, a chemist attempted the following Sw2 reaction on a structurally complex substrate: KCN (expected) The next step in the sequence was a nitile reduction, a reaction you learned in lecture 5 that converts the -CN of a nitrile into a primary amine, -CH2NH2, as shown below: CN NH2 . LiAIH4. Et O 2. NH4CI (expected) (nitrile reduction) (expected) However, distinct amine products formed, which implies (since the nitrile reduction above does not affect stereochemistry) that there were actually two nitrile products formed from the very first substitution reaction! The chemist immediately suspected that the substitution did not proceed with complete inversion as expected. when the chemist analyzed the product, it was found that there were actually two a. Assuming that the chemist is correct and the substitution did not proceed with complete inversion, draw the two products that would result from the reaction above. b. What is the specific relationship between the products in part (a), and how might this help the chemist understand how to separate them? c. Provide a brief explanation for why the original substitution reaction did not proceed exclusively with inversion of stereochemistry as expected.

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