Ask Experts Questions for FREE Help !
    markvella's Avatar
    markvella Posts: 1, Reputation: 1
    New Member

    Apr 9, 2007, 04:55 AM
    Organic Chemistry
    Why does the hydrolysis of 2-iodobutane give a single optical isomer as organic product whereas the hydrolysis of 2-methyl-2-iodohexane gives a mixture of 2 optical isomers?
    kp2171's Avatar
    kp2171 Posts: 5,318, Reputation: 1612
    Uber Member

    Apr 12, 2007, 10:41 PM
    I don't see it. Are you sure the names and info is correct?

    I'm assuming by hydrolysis you are talking about substitution of the halide with OH.

    2-iodobutane would produce an optically active isomer in forming 2-butanol. But id expect a polar, protic nucleophile to force SN1 products... granted, it's a secondary alkyl halide, but you'd still get at least a mixture of both R/S isomers. Its common to see both sn1 and sn2 products with secondary r-x's. So unless I'm missing something, and maybe I am, I think you'd see two optically active isomers of 2-butanol for the first case.

    the second one also confuses me a bit. Assuming again that you do a substitution reaction on this compound, a tertiary alkyl halide, you'd definitely expect a carbocation mechanism in a protic solvent... but... the reaction site isn't chiral. There are two methyl groups off the second carbon... so after the h2o adds, there is no chiral product at all. Again, maybe I'm missing something.

    do you have more info about this question or the answer?

Not your question? Ask your question View similar questions


Question Tools Search this Question
Search this Question:

Advanced Search

Check out some similar questions!

Organic Gardening [ 5 Answers ]

My husband and I are going to start an organic garden... but need some direction. Since we are beginners, would anyone recommend a book that is highly useful for this great hobby? Now we aren't trying to grow a farm... just something to feed the family. Thanks... ;)

Question on structures in Organic Chemistry ! [ 2 Answers ]

3.52 mg of compound "A" reacts with red Phosphorous and Bromine to gine compound "B". Compound "B" on reaction with KCN fives "C" which on hydolysis gives "D". "D" is optically inactive. "D" on mild heating gives "E" & "F". "E" on further heating in presence of Soda Lime gived "F" & "G". Both "F"...

Organic Chemistry - Clemmensen reduction [ 3 Answers ]

Hi! I REALLY REALLY need to know the mechanism for the Clemmensen Reduction of ketones/aldehydes using Zn(Hg) + HCl!? How do the electrons transfer to reduce ketones/aldehydes to alkanes? I have an exam soon! Your help will be much appreciated!

Organic chemistry [ 2 Answers ]

How can 2-ethylcyclohexane be converted to 1-ethylcyclohexanol and 2-ethylcyclohexanol?

View more questions Search