Home
Class 12
CHEMISTRY
(Z) -3- bromo -3- hexene when treated wi...

(Z) -3- bromo -3- hexene when treated with `CH_(3)O^(-)" in "CH_(3)OH` gives

A

3 - hexyne

B

2 - hexyne

C

2, 3 - hexadiene

D

2, 4 - hexadiene

Text Solution

AI Generated Solution

The correct Answer is:
To solve the question regarding the reaction of (Z)-3-bromo-3-hexene with CH₃O⁻ in CH₃OH, we can follow these steps: ### Step 1: Identify the Structure of (Z)-3-bromo-3-hexene - (Z)-3-bromo-3-hexene has a double bond at the 3rd carbon, with a bromine atom attached to the same carbon. The structure can be represented as follows: ``` CH3-CH2-C(Br)=C(CH3)-CH2-CH3 ``` - The (Z) configuration indicates that the higher priority groups (the bromine and the ethyl group) are on the same side of the double bond. ### Step 2: Recognize the Role of CH₃O⁻ - CH₃O⁻ (methoxide ion) is a strong base and will act to deprotonate the more acidic hydrogen atom adjacent to the double bond. ### Step 3: Determine the Acidic Proton - The acidic protons are those on the sp² carbon (the carbon involved in the double bond). In this case, the hydrogen atom on the carbon adjacent to the bromine (C-2) is more acidic than the one on the sp³ carbon (C-4) due to the higher s-character of sp² hybridized carbons. ### Step 4: Deprotonation - The methoxide ion will abstract the acidic proton from the sp² carbon (C-2), resulting in the formation of a carbanion at the C-2 position: ``` CH3-CH2-C(-)=C(Br)-CH2-CH3 ``` ### Step 5: Bromine as a Leaving Group - The carbanion formed is now a good nucleophile. The bromine atom (Br) is a good leaving group and will leave, allowing the double bond to shift and form a triple bond between C-2 and C-3. ### Step 6: Formation of the Final Product - After bromine leaves, the double bond shifts to form a triple bond, resulting in the final product, which is 3-hexyne: ``` CH3-CH2-C≡C-CH2-CH3 ``` ### Conclusion - The final product of the reaction is 3-hexyne. ### Final Answer The product formed when (Z)-3-bromo-3-hexene is treated with CH₃O⁻ in CH₃OH is **3-hexyne**. ---
Promotional Banner

Similar Questions

Explore conceptually related problems

Give reasons for the following : (i) Phenol is more acidic than methanol. (ii) The C-O-H bond angle in alcohols is slightly less than the tetrahedral angle (109^(@)28'). (iii) (CH_(3))_(3) C-O-CH_(3)" on reaction with HI gives "(CH_(3))_(3)C-I and CH_(3)-OH" as the main products and not "(CH_(3))_(3) C-OH and CH_(3)-I.

(CH_(3))_(3)C-OCH_(3) on reaction with HI gives (CH_(3))_(3)C-I and CH_(3)-OH as the main products and not (CH_(3))_(3)C-OH and CH_(3)-I . Explain.

CH_(3)-CH_(2)=N=O and CH_(3)-CH=N-OH are:

The major product obtained on treatment of CH_(3)CH_(2)CH(F) CH_(3) " with " CH_(3)O^(-)//CH_(3)OH is :

Glucose when treated with CH_3 OH in the presence of dry HCl gives alpha and beta -methylglucosides because it contains

When CH_(3)OH(l) is mixed in water:

Place the following alcohols in decreasing order of rate of dehydration with H_(2)SO_(4) . CH_(3)CH_(2)CHunderset((1))((OH))CH_(2)CH_(2)CH_(3) (CH_(3))_(2)Cunderset((2))((OH))CH_(2)CH_(2)CH_(3) (CH_(3))_(2)Cunderset((3))((OH))CH(CH_(3))_(2) CH_(3)CH_(2)CHunderset((4))((OH))CH(CH_(3))_(2) CH_(3)CH_(2)CH_(2)underset((5))(CH_(2))CH_(2)CH_(2)OH

Which compound is formed when CH_(3)OH reacts with CH_(3)MgX ?

Arrange the following in order of their Increasing basicity: H_(2)O, OH^(-), CH_(3)OH, CH_(3)O^(-)