Identify reagents that can be used to convert 1-pentyne into 1-bromopentane.Select answer from the options below1) HBr (1 equiv.); 2) H2, Pd1) H2, Lindlar's catalyst; 2) HBr (1 equiv.), ROOR1) H2, Lindlar's catalyst; 2) HCl (1 equiv.)1) HBr (1 equiv.); 2) H2, Lindlar's catalyst1) HBr (1 equiv.), ROOR; 2) H2, Lindlar's catalyst
Question
Identify reagents that can be used to convert 1-pentyne into 1-bromopentane.Select answer from the options below1) HBr (1 equiv.); 2) H2, Pd1) H2, Lindlar's catalyst; 2) HBr (1 equiv.), ROOR1) H2, Lindlar's catalyst; 2) HCl (1 equiv.)1) HBr (1 equiv.); 2) H2, Lindlar's catalyst1) HBr (1 equiv.), ROOR; 2) H2, Lindlar's catalyst
Solution
The correct answer is: 1) H2, Lindlar's catalyst; 2) HBr (1 equiv.), ROOR
Here's the step-by-step explanation:
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The 1-pentyne is first hydrogenated using H2 and Lindlar's catalyst. Lindlar's catalyst is a poisoned catalyst that allows for the selective hydrogenation of alkynes to alkenes (cis-alkenes specifically). This step will convert 1-pentyne into 1-pentene.
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The 1-pentene is then reacted with HBr in the presence of a peroxide (ROOR). This is a radical reaction, and it follows the anti-Markovnikov rule, which means that the bromine will add to the less substituted carbon of the alkene. This will give us 1-bromopentane.
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