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. neutralized by the tertiary amine tertiary amine RCH,OH Ph,CCI RCH,OCP., HCI Triphenylmethyl chloride (Trityl chloride) A triphenylmethyl ether (A trityl ether) Triphenylmethyl ethers are stable to aqueous base but are rapidly cleaved in aqueous acid. RCH,OCPH3 + H2O RCH2OH + Ph3COH

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How might the structure of the triphenylmethyl group be modified to increase or decrease its acid sensitivity?

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.
neutralized by the
tertiary amine
tertiary
amine
RCH,OH
Ph,CCI
RCH,OCP.,
HCI
Triphenylmethyl chloride
(Trityl chloride)
A triphenylmethyl ether
(A trityl ether)
Triphenylmethyl ethers are stable to aqueous base but are rapidly cleaved in aqueous acid.
RCH,OCPH3 + H2O
RCH2OH + Ph3COH
Transcribed Image Text: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. neutralized by the tertiary amine tertiary amine RCH,OH Ph,CCI RCH,OCP., HCI Triphenylmethyl chloride (Trityl chloride) A triphenylmethyl ether (A trityl ether) Triphenylmethyl ethers are stable to aqueous base but are rapidly cleaved in aqueous acid. RCH,OCPH3 + H2O RCH2OH + Ph3COH
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