Practicing Success
Ethers are class of organic compounds that contain ether group – an oxygen atom connected to two alkyl groups or aryl groups. They have the general formula R – O – R′, where R and R′ represents the alkyl or aryl groups. Ether, like water have a tetrahedral geometry i.e., oxygen is sp3 hybridised. The C – O – C bond angle in ethers is slightly greater than the tetrahedral angle due to repulsive interactions between the two bulky groups when they are attached to oxygen. |
Dehydration of alcohol to ethers is catalyzed by: |
Conc. \(H_2SO_4\) at 413 K Hot & \(NaOH\) Hot & \(HBr\) Hot & \(HNO_3\) |
Conc. \(H_2SO_4\) at 413 K |
The correct answer is option 1. Conc. \(H_2SO_4\) at 413 K. Symmetrical ethers can be made from the acid-catalyzed dehydration of primary alcohols. A classic example is the heating of ethanol at 130-140 °C to give diethyl ether. The reaction proceeds through the protonation of a hydroxyl group to give the conjugate acid followed by an \(S_N2\) reaction to give the symmetrical ether. The process works best for making symmetrical ethers of primary alcohols. Mechanism: Synthesis Of Symmetrical Ethers via Acid-Catalyzed Dehydration of Alcohols There are three key steps. First of all, one equivalent of alcohol is protonated to its conjugate acid – which has the good leaving group, \(OH_2\) (water, a weak base). Next, another equivalent of the alcohol can now perform nucleophilic attack at carbon \((S_N2)\), leading to displacement of \(OH_2\) (water) and formation of a new \(C-O\) bond. This is an \(SN_2\) reaction. The final step is deprotonation of the product by another equivalent of solvent (or other weak base), resulting in our ether product. |