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Chapter 28: Q28-11P (page 959)

p-Dimethoxytrityl (DMT) ethers are easily cleaved by mild acid treatment. Show the mechanism of the cleavage reaction.

Short Answer

Expert verified

The mechanism of the cleavage reaction can be shown:

Step by step solution

01

Definition of detritylation

The detritylation can be denoted as a p-Dimethoxtrityl protective group that can be taken out of acid Cl3COOH and its process. The reaction will take place by the SN1 mechanism. The support of the silica bounded mechanism has a 5鈥�- DMT protecting group. The main function is to protect the polymerization during the formation of resin.

02

Steps of the cleavage reaction mechanism

In step 1, the attack of oxygen lone pairs with trichloroacetic acid in dichloromethane and forms tertiary carbocation. The tertiary carbocation will increase the reaction rate and highly stable.

In step 2, the attack of the nucleophile on benzylic dimethoxytrityl cation will give the final product.

03

Overall reaction 

The overall reaction will occur by the stable carbocation formation by the SN1 mechanism. The overall reaction can be,

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Most popular questions from this chapter

Question: From what DNA sequences were each of the mRNA codons in problem 28-26 transcribed?

  1. AAU
  2. GAG
  3. UCC
  4. CAU

Question: What amino acid sequence is coded for by the following mRNA basesequence?
(5') CUA-GAC-CGU-UCC-AAG-UGA (3')

Question: Human and horse insulin both have two polypeptide chains, with one chain containing 21 amino acids and the other containing 30 amino acids. They differ in primary structure in two places. At position 9 in one chain, human insulin has Ser, and horse insulin has Gly; at position 30 in the other chain, human insulin has Thr, and horse insulin has Ala. How must the DNA for the two insulins differ?

Question: The DNA of sea urchins contains about 32% A. What percentages of the other three bases would you expect in sea urchin DNA? Explain.

Question: What anticodon sequences of tRNAs are coded for by the codons are :

  1. AAU
  2. GAG
  3. UCC
  4. CAU
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