Sign up for free to keep watching this solution

Video Solution: Assuming that the rate-determining step in the reaction of 2...

Problem

Assuming that the rate-determining step in the reaction of 2-methyl-2-butanol with hydrogen chloride to give 2-chloro-2-methylbutane is unimolecular, write an equation for this step. Use curved arrows to show the flow of electrons. 

Video Transcript

Hey everyone in this question we're looking at our compound and the reaction that took place from our 2-methyl 2-butanol and we're looking at it reacting with HCl to go with a 2-chloro 2-methyl butane. Now, the rate determining step it tells us in a uni molecular one and it should make sense to us because we have a tertiary alcohol reacting here, so we're going to have a step that's involved where our alcohol becomes protonated, so we're going to get a compound that looks like this where we have our methyl still there but now we have a water, okay? In the reaction that it wants us to draw is our water breaking off to form a carbocation, so what that's going to look like is something like this where it looks like we can't even see our oxygen, so let's redraw it, there it is with a positive charge, we know that we're going to turn our alcohol into a good leaving group for this problem, which is a water and that's going to break off on its own, what's going to happen next is from there we're going to get a carbocation. So, here's our methyl group again, here is our tertiary carbocation, okay? From there what's going to happen is our Cl minus is going to come in and simply attack and notice how we're going to get to our final product, so this is the rate determining step for this unimolecular reaction and is going to proceed through an SN1 type mechanism, alright? so I hope this made sense and let me know if you guys have any questions.

Related Practice Problems

Complete the following mechanism for an SN1 reaction that occurs when 2-chloro...

Complete the following mechanism for an SN1 reaction that occurs when 2-chloro...

Rank the following alkyl halides in order of increasing SN1 reactivity. (1 ...

Rank the following alkyl halides in order of increasing SN1 reactivity. (1 ...

Predict the organic product of the following reaction. When appropriate, ...

Predict the organic product of the following reaction. When appropriate, ...

Rank the following molecules in increasing order of susceptibility to an SN1 r...

Rank the following molecules in increasing order of susceptibility to an SN1 r...

Using arrows to show the flow of electrons, write a stepwise mechanism for the...

Using arrows to show the flow of electrons, write a stepwise mechanism for the...

Energy Diagram and Features of SN1 Reactions
...

Energy Diagram and Features of SN1 Reactions ...

 Provide the major product for the following reaction. 
...

 Provide the major product for the following reaction.  ...

Draw the mechanism for each of the following reactions: 
...

Draw the mechanism for each of the following reactions:  ...

Draw the mechanism for each of the following reactions: 
...

Draw the mechanism for each of the following reactions:  ...

Draw the mechanism of the following SN1 processes: 
...

Draw the mechanism of the following SN1 processes:  ...

Draw the mechanism of the following SN1 processes: 
...

Draw the mechanism of the following SN1 processes:  ...

Draw the mechanism of the following SN1 processes: 
...

Draw the mechanism of the following SN1 processes:  ...

Draw the mechanism for the following SN1 reaction
...

Draw the mechanism for the following SN1 reaction ...

Predict the product(s) for the following reaction.
...

Predict the product(s) for the following reaction. ...

A) Provide structures in the box to complete the Lewis acid-base reaction....

A) Provide structures in the box to complete the Lewis acid-base reaction....

For each of the following sets of molecules, CIRCLE the set that will undergo ...

For each of the following sets of molecules, CIRCLE the set that will undergo ...

How many atoms and electrons are directly involved in the bond-making and...

How many atoms and electrons are directly involved in the bond-making and...

Draw the mechanism for the solvolysis of (R)-3-iodo-3-methylhexane in water, l...

Draw the mechanism for the solvolysis of (R)-3-iodo-3-methylhexane in water, l...

Draw the reaction mechanism and the energy diagram for the following substitut...

Draw the reaction mechanism and the energy diagram for the following substitut...

What set of reaction conditions would favor an SN1 reaction on 2-bromo-3-methy...

What set of reaction conditions would favor an SN1 reaction on 2-bromo-3-methy...

Draw the structure(s) of the product(s) that you would expect from t...

Draw the structure(s) of the product(s) that you would expect from t...

Use A-G to label the graph with the structures given for the reaction:

 ...

Use A-G to label the graph with the structures given for the reaction:  ...

The hybridization state of the charged carbon in an S N1 reaction is:


	...

The hybridization state of the charged carbon in an S N1 reaction is: ...

Compare the following reactions and decide which reaction in each pair would o...

Compare the following reactions and decide which reaction in each pair would o...