Reactivity of alkanes and alkenes (1 Viewer)

cko

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I did accelerated chem and then i repeated, so i also had to repeat the prac wher u have to compare the reactivity of alkanes and alkenes. Except when i did it the second time around (with a different teacher) the reaction were totally different! Now i don't know what to do.

with the prac that i did in yr 11:

(hexane) CH3-CH2-CH2-CH2-CH2-CH3 + BrOH --> CH2Br-CH2-CH2CH2-CH2-CH3 + WATER


but in the prac that i did this year:
(hexane) CH3-CH2-CH2-CH2-CH2-CH3 + BrOH --> CH2Br-CHOH-CH2-CH2-CH2-CH3 + H2

I don't know what to do!!! Which one is the correct one????
 
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cko

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kim that thread doesn't particularly answer my question!!! Actually im more confused than ever! people keep saying different things!!!
 

cko

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aaaargh i reall REALLY need an answer ASAP!! My half yearly exam is TOMORROW!!!!!!!
 

CM_Tutor

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Cko, I will sort out the questions on the bromine water tests later today. In the meantime, could you re-post your equations in condensed structural form (ie CH<sub>3</sub>-CH<sub>2</sub>- ... etc), or molecular form (ie. C<sub>6</sub>H<sub>14</sub> + Br<sub>2</sub>) because the one you have at present is confusing.
 

xiao1985

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cm tutor, i think:

the first one: the first one, only one hydrogen in the hydrocarbon has being replaced by Br ...

in the second one, two adjacent hydrocarbons are replaced by Br and OH respectively...

i believe the first one was right... because i think only halogens react with alkanes with the presense of uv...
 

CM_Tutor

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OK, assuming xiao1985 is correct and this is supposed to indicate the reactions of an alkane with bromine in the presence of UV light, then NEITHER equation is correct.

The substitution reaction should be:

hexane + bromine ---UV Light---> an isomer of bromohexane + hydrobromic acid

Note that by an isomer of bromohexane, I mean one of 1-bromohexane, 2-bromohexane or 3-bromohexane. In any of these cases, the reaction will have a molecular equation of:

C<sub>6</sub>H<sub>14</sub> + Br<sub>2</sub> ---UV Light---> C<sub>6</sub>H<sub>13</sub>Br + HBr

This reaction is NOT subject to the debate about the nature of bromine water that I have discussed in the other thread on this topic for the reaction of bromine water with alkenes. The reaction of a halogen with an alkane follows a radical chain reaction mechanism which requires a halogen (X<sub>2</sub>) as a reacting species. Neither a hydrohalic acid (HX) nor any oxyhalic acid (HOX<sub>n</sub>, where n = 1, 3, 5 or 7) is an acceptable substitute in this mechanism.

Assuming that you MUST use one of these equations, then I would say that the first is objectionable, and the second is ridiculous / preposterous / absurd / chemically evil / ... . The reason is that there is NO WAY that a system like the one described would produce hydrogen gas as a product, and this could easily be demonstrated by noting that no bubbles form in the reaction mixture.

A further note: Assuming that the reaction is in the absence of UV light, then there is no way ANY reaction will take place. Alkanes do not undergo substitution reactions under anything but fairly extreme conditions. If anyone can find a way to make alkanes into a product like a haloalkane or a haloalkanol in a controlled way under mild conditions - such as is suggested by these equations in the absence of UV - then that person is well on their way to a Nobel Prize. :)

CKO: I will chack back on this thread later tonight if you want to post any other questions about this before your exam tomorrow, and in any case, good luck!
 

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