Predict the two most likely mechanisms for the reaction of 1-iodohexane with potassium tert-butoxide.

Chemistry

1 answer:

Rudiy273 years ago

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Answer:

C) SN2 and E2

Explanation:

For this question, we have analyzed the substrate and the base/nucleophile. The substrate, in this case, is 1-iodohexane and the base/nucleophile is potassium tert-butoxide.

Substrate

In the 1-iodohexane the iodide "I" is bonded to a primary carbon (carbon 1). Therefore we will have a primary substrate. If we have a primary substrate an Sn1 can not take place. We can not have a primary carbocation due to this instability. So, we can disccard options A) and B).

Base/nucleophile

In the potassium tert-butoxide we have an ionic compound. A positive charge is placed in the potassium atom a negative charge is placed in the oxygen of the ter-butoxide ion. So, we will have a strong base (a molecule with the ability to remove electrons) and a strong nucleophile (a molecule with ability to bond with an electrophile). With all this in mind, we can not have an E1 reaction.

With both analyses, the answer is C).

See figure 1

I hope it helps!

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choose any bases that will selectively deprotonate the above acid, that is, any bases that will favor the formation of products.

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In order to deprotonate an acid, we must remove protons in order to achieve a more stable conjugate base. For this example, we can use the relationship between carboxylic acid and hydroxide.

Deprotonation is the removal of a proton from a specific type of acid in reaction to its coming into contact with a strong base. The compound formed from this reaction is known as the conjugate base of that acid. The opposite process is also possible and is when a proton is added to a special kind of base. This is a process referred to as protonation, which forms the conjugate acid of that base.

For the example we have chosen to give, the conjugate base is the carboxylate salt. This would be the compound formed by the deprotonated carboxylic acid. The base in question was strong enough to deprotonate the acid due to the greater stability offered as a conjugated base.

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