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- Apr 6, 2014
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The question reads: When treated with aqueous hydrochloric acid, the Grape Berry Moth sex pheromone in Figure 1 would yield:
A. a diene
B. an ester and an alcohol
C. a carboxylic acid and an alcohol
D. a carboxylic acid and an ether.
Here is the structure of the pheromone:
http://tinypic.com/r/15555r8/8
The book says the correct answer is C, and these would be the molecules it'd yield:
http://tinypic.com/r/b7xkiu/8
But wouldn't it yield a carboxylic acid and a diol, or a carboxylic acid and 9-chlorododecanol? Doesn't dilute acid replace a double bond with an alcohol? I've typically seen double bond hydration reactions done with dilute h2so4, but HCl is a strong acid, too, and should thus yield the same products. And if that's not the case, the double bond should definitely have gone through electrophilic addition and been replaced with a chlorine... Right?
A. a diene
B. an ester and an alcohol
C. a carboxylic acid and an alcohol
D. a carboxylic acid and an ether.
Here is the structure of the pheromone:
http://tinypic.com/r/15555r8/8
The book says the correct answer is C, and these would be the molecules it'd yield:
http://tinypic.com/r/b7xkiu/8
But wouldn't it yield a carboxylic acid and a diol, or a carboxylic acid and 9-chlorododecanol? Doesn't dilute acid replace a double bond with an alcohol? I've typically seen double bond hydration reactions done with dilute h2so4, but HCl is a strong acid, too, and should thus yield the same products. And if that's not the case, the double bond should definitely have gone through electrophilic addition and been replaced with a chlorine... Right?