21E - Organic Chemistry (Mcmurry)

Question

Predict the product(s) and provide the mechanism for each reaction below.

Step-by-Step Solution

Answer

Step 1: Product of the reaction

The product of the reaction is 2-bromobutanal

Step 2: Mechanism of the reaction

Step 3: Explanation of the mechanism

The carbonyl oxygen of the butanal is protonated by acetic acid.

Then the protonated form loses a proton and becomes an enol.

Then the double bond of the enol attacks the bromine-bromine bond and removes a bromide ion.

Then the bromide ion deprotonated it and yielded our desired product.

Step 4: Conclusion

Hence the complete reaction is 

 

Answer of subpart (b): Step 5: Product of the reaction

The product of the reaction is 2-chlorocyclohexanone.

 

Step 6: Mechanism of the reaction

Step 7: Explanation of the mechanism

 

The carbonyl oxygen of the cyclohexanone is protonated by acetic acid.

Then the protonated form loses a proton and becomes an enol.

Then the double bond of the enol attacks the chlorine-chlorine bond and removes a chloride ion.

Then the chloride ion deprotonated it and yielded our desired product.

 

 

Step 8: Conclusion

Hence the complete reaction is 

Step 9: (c) Product of the reaction

The product of the reaction is iodomethyl phenyl ketone.

Step 10: Mechanism of the reaction

Step 11: Explanation of the mechanism

The carbonyl oxygen of the acetophenone is protonated by acetic acid.

Then the protonated form loses a proton and becomes an enol.

Then the double bond of the enol attacks the iodine-iodine bond and removes an iodide ion.

Then the iodide ion deprotonated it and yielded our desired product.

 

Step 12: Conclusion

Hence the complete reaction is 

 

Step 13: (d) Product of the reaction

The product of the reaction is 1-bromo-3,3-dimethyl-2-butanone.

 

Step 14: Mechanism of the reaction

Step 15: Explanation of the mechanism

The carbonyl oxygen of the 3,3-dimethyl-2-butanone is protonated by acetic acid.

Then the protonated form loses a proton and becomes an enol.

Then the double bond of the enol attacks the bromine-bromine bond and removes a bromide ion.

Then the bromide ion deprotonated it and yielded our desired product.

 

Step 16: Conclusion

Hence the complete reaction is