Organic chemistry acetal reaction help

[IntegralDerivative]

<Moderator's note: Moved from a technical forum and thus no template.>

OChem Question:

My Answer:

Not sure if this is correct. Anyone?

 

[TeethWhitener]

What's your reasoning for the cyclohexanol hosting an acetal carbon?

Edit: is this homework? If so, it belongs in the homework forums.

 

[IntegralDerivative]

What's your reasoning for the cyclohexanol hosting an acetal carbon?

Edit: is this homework? If so, it belongs in the homework forums.

Cyclohexanol is larger. I think it could go either way. Are there major and minor products here? Sorry I thought this was the homework forum. How do I move this thread?

 

[TeethWhitener]

I asked the mods to migrate the thread. Meanwhile, can you tell me how to make an acetal? What functional groups are required?

 

[IntegralDerivative]

I asked the mods to migrate the thread. Meanwhile, can you tell me how to make an acetal? What functional groups are required?

Thank you so much. You need alcohols, a leaving group (like H2O) and acid catalyst to make an acetal.

 

[TeethWhitener]

Thank you so much. You need alcohols, a leaving group (like H2O) and acid catalyst to make an acetal.

Alcohol and? What other organic functionality do you need?

 

[IntegralDerivative]

Alcohol and? What other organic functionality do you need?

Carbonyl group?

 

[TeethWhitener]

Yes. If you have a carbonyl group, what happens if you add one equivalent of alcohol? (Formally, ignoring equilibrium considerations) Do you get an acetal right off the bat?

 

[IntegralDerivative]

Yes. If you have a carbonyl group, what happens if you add one equivalent of alcohol? (Formally, ignoring equilibrium considerations) Do you get an acetal right off the bat?

You will get a hemiacetal. But I thought you need oxidizing agents to turn alcohols into carbonyls? How do we get a carbonyl in this case with only sulfuric acid?

 

[TeethWhitener]

You will get a hemiacetal. But I thought you need oxidizing agents to turn alcohols into carbonyls? How do we get a carbonyl in this case with only sulfuric acid?

You're getting ahead of yourself. Look at your original problem and tell me what functionalities you have.
Edit: hemiacetal is right (and is the important part). The rest of the post veers off the path a little.

 

[IntegralDerivative]

You're getting ahead of yourself. Look at your original problem and tell me what functionalities you have.
Edit: hemiacetal is right (and is the important part). The rest of the post veers off the path a little.

I see. So the hemiacetal is the

. and so it will form a carbonyl after the H2O group leaves and then the cyclohexanol will attack to the carbonyl carbon?

Do you know how to name the

molecule?

 

[TeethWhitener]

I see. So the hemiacetal is the View attachment 212179 . and so it will form a carbonyl after the H2O group leaves and then the cyclohexanol will attack to the carbonyl carbon?

Do you know how to name the View attachment 212179 molecule?

You've added a step. "Hemiacetal" literally means "half an acetal." Meaning you're already halfway to an acetal. Take another stab at it.

 

[IntegralDerivative]

You've added a step. "Hemiacetal" literally means "half an acetal." Meaning you're already halfway to an acetal. Take another stab at it.

I am not sure what you mean. I described these steps here I think:

 

[TeethWhitener]

I am not sure what you mean. I described these steps here I think:

View attachment 212181

Ah I see what you're saying. That's an oxonium, not a carbonyl. Yes, these are the steps you want. So what's your final product?

 

[IntegralDerivative]

Ah I see what you're saying. That's an oxonium, not a carbonyl. Yes, these are the steps you want. So what's your final product?

This:

 

[TeethWhitener]

Good work.

This: View attachment 212182

 

[IntegralDerivative]

Good work.

Thank you so much!