In the chemical synthesis of DNA and RNA, hydroxyl groups

Chapter 21, Problem 21.48

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In the chemical synthesis of DNA and RNA, hydroxyl groups are normally converted to triphenylmethyl (trityl) ethers to protect the hydroxyl group from reaction with other reagents. tertiary amine RCH2OH 1 Ph3CCl RCH2OCPh3 HCl Triphenylmethyl chloride (Trityl chloride) A triphenylmethyl ether (A trityl ether) 1 neutralized by the tertiary amine Triphenylmethyl ethers are stable to aqueous base but are rapidly cleaved in aqueous acid. RCH2OCPh3 1 H2O RCH 9: 2OH 1 Ph3COH H1 (a) Why are triphenylmethyl ethers so readily hydrolyzed by aqueous acid? (b) How might the structure of the triphenylmethyl group be modifi ed to increase or decrease its acid sensitivity?

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