In the given reaction
3-Bromo-2, 2-dimethyl butane \(\xrightarrow{\mathrm{C_2H_5OH}}\) 'A' (Major Product)
Product A is :
3-Bromo-2, 2-dimethyl butane \(\xrightarrow{\mathrm{C_2H_5OH}}\) 'A' (Major Product)
Product A is :
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- 2-Ethoxy-3, 3-dimethyl butane
- 1-Ethoxy-3, 3-dimethyl butane
- 2-Ethoxy-2, 3-dimethyl butane
- 2-Hydroxy-3, 3-dimethyl butane
The Correct Option is C
Solution and Explanation
In \(\mathrm{C_2H_5OH}\) the bromide ionises (SN1) to the secondary carbocation \(\mathrm{CH_3-CH^+-C(CH_3)_3}\).
A 1,2-methyl shift from the quaternary carbon gives the more stable tertiary carbocation \(\mathrm{(CH_3)_2CH-C^+(CH_3)_2}\).
Ethanol attacks this cation and loses \(\mathrm{H^+}\) to give \(\mathrm{(CH_3)_2CH-C(CH_3)_2-OC_2H_5}\), named 2-ethoxy-2,3-dimethylbutane.
Option (1) (unrearranged, from the secondary cation) is the minor product, option (2) cannot form, and option (4) has an OH which cannot come from ethanol.
Answer: (3) 2-Ethoxy-2, 3-dimethyl butane
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