Why must alkylation reactions be done in completely anhydrousconditions? also...

Question

Why must alkylation reactions be done in completely anhydrousconditions? also....What alkene should be used to obtain4-bromo-4-methylheptane as the only product? 1. 2-methyl-3-heptene    2. 3-methyl-3heptene 3. 4-methyl-3-heptene 4. 4-methyl-2-heptene I know it involves a methyl shift but I can't seem tounderstand it. Please provide me with some steps so I can seeit! Why must alkylation reactions be done in completely anhydrousconditions? also....What alkene should be used to obtain4-bromo-4-methylheptane as the only product? 1. 2-methyl-3-heptene    2. 3-methyl-3heptene 3. 4-methyl-3-heptene 4. 4-methyl-2-heptene I know it involves a methyl shift but I can't seem tounderstand it. Please provide me with some steps so I can seeit!

Explanation / Answer

Many alkylations are performed using Grignards or othernucleophiles. However, nucleophiles can also act as bases in thepresence of water to abstract a proton from the water molecule,resulting in undesired side products and deactivatednucleophiles. For the second question, I believe the answer is 3. 4-methyl-3-heptene There is no methyl shift. The reaction follows the additionmechanism and Markonikov orientation. The carbocation is formed onthe most substitued carbon of the double bond, C4, and the halogenadds to the carbon with the least number of hydrogens, which isC4.

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