1.The Ether cleavage reaction is another Sn reaction where the ether is first pr
ID: 489498 • Letter: 1
Question
1.The Ether cleavage reaction is another Sn reaction where the ether is first protonated to create an oxonium ion leaving group. The conjugated base from the acid used in the first protonation step is then used as a nucleophile in the substitution. What makes these reactions different from the typical Sn reaction is that for many ethers, there can be two substrate carbons where the nucleophile can attach. Considering the Sn ether cleavage reaction, which of the following ethers will yield only two different organic products when reacted with excess HCL?
2. Which synthetic pathway below gives a racemic mixture of the following deuterated compound?
Explanation / Answer
1. Symmetrical ethers and cyclic ethers give same products when reacted with excess of HCl. So, compound B and D will give two different products.
2. All the above reactions will give racemix mixture of deuerated compound.
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