CH30 K,CO3 N. DMF several HO. steps он но raloxifene

Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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 Drawing an SN2 product with More Complex Reactants

Identify C, the product of an SN2 reaction in the synthesis of raloxifene, a drug used to reduce the risk of invasive breast cancer in postmenopausal women.

CH30
K,CO3
N.
DMF
several
HO.
steps
он
но
raloxifene
Transcribed Image Text:CH30 K,CO3 N. DMF several HO. steps он но raloxifene
Expert Solution
Step 1

In the given reaction, both the starting materials have two functional groups we just need to follow a simpler reactions strategy in this :

1)First we need to identify the leaving group and attacking nucleophile. The second reactant contains a Cl bond which is bonded to an SPhybridized carbon atom, which acts as a leaving group while the first reactant acts as a nucleophile.

       As the reaction carried out in the presence of K2CO3 which is a base so it will remove the most acidic proton from the reactant and in this case it is the OH group from the first reactant. Removal of OH proton in the first reactant will form the negatively charged conjugate base which acts as a nucleophile.

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