What is good about using bulky borane in alkyne reaction?

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In summary, using bulky borane (9BBN) for hydroboration of alkynes has two main advantages: increased steric bulk for more efficient reactions and improved safety due to its stability compared to other borane compounds.
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Homework Statement


Give two advantageous reasons for using bulky borane (9BBN) for hydroboration of alkynes.

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The Attempt at a Solution


I'm thinking it might have to do with the size of alkynes and bulky reagents, but I'm really not sure.
 
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1. Using 9BBN for hydroboration of alkynes is advantageous because it provides a larger steric bulk, which allows for the reaction to take place in a more efficient manner and with less steric hindrance compared to other reagents.2. 9BBN is also advantageous for hydroboration of alkynes because it is more stable than other borane compounds, making it a safer reagent to use in the reaction.
 

1. What is the purpose of using bulky borane in alkyne reactions?

Bulky borane, such as disiamylborane (DIBAL), is used in alkyne reactions as a selective reducing agent. It allows for the reduction of alkyne functional groups without affecting other functional groups present in the molecule.

2. How does bulky borane differ from other reducing agents commonly used in alkyne reactions?

Bulky borane, unlike other reducing agents such as lithium aluminum hydride, is able to reduce alkyne functional groups without the formation of unstable intermediates. This makes it a safer and more efficient option for alkyne reductions.

3. Can bulky borane be used in all types of alkyne reactions?

While bulky borane is commonly used in alkyne reductions, it can also be used in other types of alkyne reactions such as hydroboration and addition reactions. However, its effectiveness may vary depending on the specific reaction conditions.

4. Are there any drawbacks to using bulky borane in alkyne reactions?

One potential drawback of using bulky borane is its high cost compared to other reducing agents. Additionally, it may not be compatible with certain functional groups, so it is important to carefully consider the reaction conditions and potential side reactions.

5. How does bulky borane contribute to the overall success of alkyne reactions?

Bulky borane is a valuable tool in organic synthesis as it allows for the selective reduction of alkyne functional groups, which may be difficult to achieve with other reducing agents. Its use can also lead to higher yields and improved reaction selectivity.

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