The major product which results when 2-chloro-2-methylpentane is heated in ethanol is an ether. What is the mechanism by which this ether forms?

Answer 1
The ether forms by an #"S"_"N"1# mechanism.

The general response is

#"CH"_3"CH"_2"CH"_2"C(CH"_3")"_2"Cl" + "CH"_3"CH"_2"OH" ⇌ "CH"_3"CH"_2"CH"_2"C(CH"_3")"_2"(OCH"_2"CH"_3")" + "HCl"#
The substrate is a 3° halide, and the ethanol is both a weak nucleophile and a polar protic solvent, so the reaction will go by an #"S"_"N"1# mechanism.

There won't be any changes made as the carbocation is already at a 3° angle.

THE SYSTEM

Step 1. Loss of #"Cl"^-# to form a 3° carbocation.
#"CH"_3"CH"_2"CH"_2"C(CH"_3")"_2"Cl" → "CH"_3"CH"_2"CH"_2"C(CH"_3")"_2^+ + "Cl"^-#

Step 2: Ethanol's nucleophilic attack

#"CH"_3"CH"_2"CH"_2"C(CH"_3")"_2^+ + "CH"_3"CH"_2"OH" → "CH"_3"CH"_2"CH"_2"C(CH"_3)_2"-O"^+"(H)CH"_2"CH"_3#

Step 3: Oxonium ion deprotonation

#"CH"_3"CH"_2"CH"_2"C(CH"_3)_2"-"^+"O(H)CH"_2"CH"_3 + "CH"_3"CH"_2"-OH" → "CH"_3"CH"_2"CH"_2"C(CH"_3)_2"-OCH"_2"CH"_3 + "CH"_3"CH"_2"-OH"_2^+#
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Answer 2

The formation of ether from 2-chloro-2-methylpentane in ethanol typically proceeds via an SN1 (substitution nucleophilic unimolecular) mechanism. In this mechanism, the chlorine atom of 2-chloro-2-methylpentane is displaced by ethanol, leading to the formation of a carbocation intermediate. Subsequently, ethanol acts as a nucleophile, attacking the carbocation to form a new bond and produce the ether product. This process involves a two-step reaction: first, the formation of a carbocation intermediate, and second, the nucleophilic attack by ethanol to form the ether.

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Answer 3

The mechanism by which the ether forms when 2-chloro-2-methylpentane is heated in ethanol involves the nucleophilic substitution reaction. In this process, ethanol acts as a nucleophile attacking the carbon atom adjacent to the chlorine atom in 2-chloro-2-methylpentane. This attack displaces the chloride ion, leading to the formation of an intermediate carbocation. Subsequently, another ethanol molecule acts as a nucleophile, attacking the carbocation to form the desired ether product.

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Answer from HIX Tutor

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.

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