Initiation: R3SNH + Z. R3Sn- HZ Rortepgular SR.Sn. R': + R;SnBr Propagation: R': + R3SnH R3Sn- R'-H R3SNH Br Z. + R;SnBr

Chemistry & Chemical Reactivity
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ISBN:9781133949640
Author:John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
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Chapter24: Biochemistry
Section24.3: Nucleic Acids
Problem 1RC: 1. Which breaks down more quickly in an aqueous solution? DNA RNA
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In the presence of a radical initiator (Z•), tributyltin hydride (R3SnH, R = CH3CH2CH2CH2) reduces alkyl halides to alkanes: R′X + R3SnH → R′H + R3SnX. The mechanism consists of a radical chain process with an intermediate tin radical:

This reaction has been employed in many radical cyclization reactions. Draw a stepwise mechanism for the following reaction.

Initiation:
R3SNH +
Z.
R3Sn-
HZ
Rortepgular SR.Sn.
R': + R;SnBr
Propagation:
R': + R3SnH
R3Sn-
R'-H
Transcribed Image Text:Initiation: R3SNH + Z. R3Sn- HZ Rortepgular SR.Sn. R': + R;SnBr Propagation: R': + R3SnH R3Sn- R'-H
R3SNH
Br
Z.
+ R;SnBr
Transcribed Image Text:R3SNH Br Z. + R;SnBr
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