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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: JoeyBob on December 09, 2019, 06:57:11 PM

Title: Does ETOH go through an E1 or E2 reaction?
Post by: JoeyBob on December 09, 2019, 06:57:11 PM

Have a 3-bromo-4-dimethylhexane molecule and was wondering why it goes through E1 instead of E2 with EtOH.

Isn't this compound a strong base? Our textbook says E2 on secondary halides only occurs in the presence of a strong base. Yet this reaction goes through an E1?

Title: Re: Does ETOH go through an E1 or E2 reaction?
Post by: phth on December 09, 2019, 11:36:38 PM

Examples of E1/E2 are not cut and dry because they depend on a variety of combined effects. Ethanol is not a strong base in its neutral state. E1/SN1 are favored in polar protic solvents, can you guess why?

Title: Re: Does ETOH go through an E1 or E2 reaction?
Post by: Babcock_Hall on December 10, 2019, 10:13:48 AM

Can you explain to us how one knows that ethanol is not a strong base?  This would be of help in other problems potentially.

Title: Re: Does ETOH go through an E1 or E2 reaction?
Post by: hollytara on December 10, 2019, 12:42:50 PM

Are you perhaps confusing "EtO^- / EtOH"  With "EtOH" by itself?

Title: Re: Does ETOH go through an E1 or E2 reaction?
Post by: JoeyBob on December 11, 2019, 01:48:23 AM

Quote from: hollytara on December 10, 2019, 12:42:50 PM

Are you perhaps confusing "EtO^- / EtOH"  With "EtOH" by itself?

Yeah. So EtO- is E2 and EtOH is SN1/E1. thanks

Title: Re: Does ETOH go through an E1 or E2 reaction?
Post by: gedftsnd on January 20, 2020, 09:16:02 AM

normally Substitution reactions not elimination