Tertiary Halide heated in water... Major product?

[gangazi]

Hello my fellow future dentists

I was having this question for a long time, but had way too much things to cover that I have not yet had a chance to ask.

On Chad's quiz, "what is the major product when heated in water?" and tertiary halide is drawn.

Chad's answer says that alcohol and alkene (explanation says that impossible to have Sn1 without E1_

However, on DAT destroyer's road map when heat is added, only Elimination product is seen. Also, on Organic Chemistry as a Second Language, it says that heat favors elimination.

What is the correct answer that I should pick when I am confronted with a tertiary halide with water and WITH/WITHOUT HEAT?

thank you !

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[jdenney741]

I believe that chad is correct when he says that both sn1 and e1 both will occur. I think heat does favor elimination though.

with it being a multiple choice test you should be able to come to the answer whether they are looking for sn1 or e1 as the major product.

 

[gangazi]

I believe that chad is correct when he says that both sn1 and e1 both will occur. I think heat does favor elimination though.

with it being a multiple choice test you should be able to come to the answer whether they are looking for sn1 or e1 as the major product.

hmm okay... what are the things that lead me to guess its sn1 or e1?

because on chads answer choices were like, alcohol, alkene, alcohol and alkene lol wut

 

[Likkriue]

E1 and sn1 both happen for a lot of reactions. So it's hard to differentiate them, but heat favors the elimination reaction. E1 and sn1 won't work for primary halides and aprotic solvents.

 

[jdenney741]

hmm okay... what are the things that lead me to guess its sn1 or e1?

because on chads answer choices were like, alcohol, alkene, alcohol and alkene lol wut

Sn1 and E1 happen on tertiary halides and secondary halides. (Cannot happen on Primary). Then look at the solvent, polar protic.

Make sure you keep an eye out for Hydride and methyl shifts as well.

 

[gangazi]

Sn1 and E1 happen on tertiary halides and secondary halides. (Cannot happen on Primary). Then look at the solvent, polar protic.

Make sure you keep an eye out for Hydride and methyl shifts as well.

thanks!! I will remember that during my exam

 

[DAT Destroyer]

Hello my fellow future dentists

I was having this question for a long time, but had way too much things to cover that I have not yet had a chance to ask.

On Chad's quiz, "what is the major product when heated in water?" and tertiary halide is drawn.

Chad's answer says that alcohol and alkene (explanation says that impossible to have Sn1 without E1_

However, on DAT destroyer's road map when heat is added, only Elimination product is seen. Also, on Organic Chemistry as a Second Language, it says that heat favors elimination.

What is the correct answer that I should pick when I am confronted with a tertiary halide with water and WITH/WITHOUT HEAT?

thank you !

Indeed so, A competition ALWAYS exits between Sn1 and E1 and this drives us crazy in lab !!! Tertiary halides favor elimination especially when heated. Heating a tertiary halide in water results in BOTH alcohol and alkene. HOWEVER......the major product would usually be the alkene. There are many theoretical explanations, but we need not explore them here. If on any exam, always go with the alkene. The minor product would be the alcohol. The Temperature is critical in the real world. For example, at 65 C, we might find 64% yield from Sn1, and 36% for E1. I reference these numbers from McMurray text . However......If we use a higher temperature, we would get 80% E1 and 20% Sn1 at 150 C. Thus.....a fine point indeed. However....as I said......If you see heat and a tertiary halide BOTH products are made, but E1 is almost always the major product.

Hope this helps.

Dr. Romano