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Chem questions (rep for help)

Need help quick, Rep for help:

C) One of the isomers of C4H8 reacts with HBR to give 2 diff products, the major one of which is a chiral molecule.

i) Identify this isomer of C4H8
ii) Give the mechanism for the reaction of this isomer with HBr
iii)why is the major product Chiral, but the minor one not?
iv) Why is the chiral product the major one, and the non-chiral the minor one?
v) The major product of this addition reaction is found to be optically inactive, explain why?

Rep will come tomorrow.
Reply 1
mc_watson87
Need help quick, Rep for help:

C) One of the isomers of C4H8 reacts with HBR to give 2 diff products, the major one of which is a chiral molecule.

i) Identify this isomer of C4H8
ii) Give the mechanism for the reaction of this isomer with HBr
iii)why is the major product Chiral, but the minor one not?


i)But-1-ene, I think.

ii) It's just an electrophilic addition, forming a primary or secondary carbocation which then gets attacked by the bromide.

iii)The major product is chiral because its mirror image cannot be superimposed upon it.

Ben
Reply 2
Ben.S.
i)But-1-ene, I think.

ii) It's just an electrophilic addition, forming a primary or secondary carbocation which then gets attacked by the bromide.

iii)The major product is chiral because its mirror image cannot be superimposed upon it.

Ben

WHy would it be but-1-ene instead of 2-methylpropene
Reply 3
mc_watson87
WHy would it be but-1-ene instead of 2-methylpropene

Apologies - yes, that's what I meant to say.

Ben

[No it wasn't, damn you!]
Reply 4
Ben.S.
Apologies - yes, that's what I meant to say.

Ben

Kool, Why is it 2-methylpropene instead of but-1-ene? Why wouldn't but-1-ene form 2 diff products aswell?
Reply 5
mc_watson87
Kool, Why is it 2-methylpropene instead of but-1-ene? Why wouldn't but-1-ene form 2 diff products aswell?

It would, but you wouldn't get enantiomers.

Ben
Reply 6
mc_watson87
WHy would it be but-1-ene instead of 2-methylpropene



After the addition 2-methylpropene would not be optically active for either isomer.
Reply 7
Ralfskini
After the addition 2-methylpropene would not be optically active for either isomer.

Ah yes, it would not have any chiral carbons- ie carbons with 4 different groups attached to it.
Reply 8
hihihihi
Ah yes, it would not have any chiral carbons- ie carbons with 4 different groups attached to it.

Oh my God, I was right first time - just do the opposite of what I say.

Ben
Reply 9
mc_watson87
Need help quick, Rep for help:

C) One of the isomers of C4H8 reacts with HBR to give 2 diff products, the major one of which is a chiral molecule.

i) Identify this isomer of C4H8
ii) Give the mechanism for the reaction of this isomer with HBr
iii)why is the major product Chiral, but the minor one not?
iv) Why is the chiral product the major one, and the non-chiral the minor one?
v) The major product of this addition reaction is found to be optically inactive, explain why?

Rep will come tomorrow.

ANyone got any ideas about the last 2 questions? :smile:
Reply 10
I'll have a go
iv) Why is the chiral product the major one, and the non-chiral the minor one?
v) The major product of this addition reaction is found to be optically inactive, explain why?


iv)You can get 1-bromobutane or 2-bromobutane. The major product is 2-bromobutane "because the H from HBr prefers to go with its hydrogen friends" (I dunno the proper scientific reason behind major and minor products). Only 2-bromobutane has a chiral carbon which is carbon 2.


v) Because a racemic mixture is produced?
Reply 11
hihihihi
I'll have a go
iv) Why is the chiral product the major one, and the non-chiral the minor one?
v) The major product of this addition reaction is found to be optically inactive, explain why?


iv)You can get 1-bromobutane or 2-bromobutane. The major product is 2-bromobutane "because the H from HBr prefers to go with its hydrogen friends" (I dunno the proper scientific reason behind major and minor products). Only 2-bromobutane has a chiral carbon which is carbon 2.


v) Because a racemic mixture is produced?

Ok cool cheers.

Could ya go into wat a racemic mixture is moreso please. :smile:
Reply 12
hihihihi
I'll have a go
iv) Why is the chiral product the major one, and the non-chiral the minor one?
v) The major product of this addition reaction is found to be optically inactive, explain why?


iv)You can get 1-bromobutane or 2-bromobutane. The major product is 2-bromobutane "because the H from HBr prefers to go with its hydrogen friends" (I dunno the proper scientific reason behind major and minor products). Only 2-bromobutane has a chiral carbon which is carbon 2.


v) Because a racemic mixture is produced?


iv) The gregarious hydrogen rule works, but it isn't the reason you're expected to give! Basically, the reason reactions have major and minor (and lots of other, most of the time) products is because the formation of each is not equally favourable kinetically and/or thermodynamically. The minor product, in this case, is produced via a primary carbocation (see the mechanism) and the major is produced via a tertiary one. Tertiary > secondary > primary in stability, due to an effect known as 'sigma donation/congugation' where adjacent C-H (sigma) bonds can stabilise positive charge on the carbocation by 'donating' electron density into its empty p orbital. The more adjacent C-H bonds there are, the more stable the cation.

v) Yes, you're right here.

Ben
Reply 13
mc_watson87
Ok cool cheers.

Could ya go into wat a racemic mixture is moreso please. :smile:

It's a mixture containing equal quantities of two enantiomers - both of which have equal and opposing optical properties and so the mixture is optically inactive overall.

Ben
Reply 14
Ben.S.
It's a mixture containing equal quantities of two enantiomers - both of which have equal and opposing optical properties and so the mixture is optically inactive overall.

Ben

Cool. :smile:
Reply 15
hihihihi
I'll have a go
iv) Why is the chiral product the major one, and the non-chiral the minor one?
v) The major product of this addition reaction is found to be optically inactive, explain why?


iv)You can get 1-bromobutane or 2-bromobutane. The major product is 2-bromobutane "because the H from HBr prefers to go with its hydrogen friends" (I dunno the proper scientific reason behind major and minor products). Only 2-bromobutane has a chiral carbon which is carbon 2.


v) Because a racemic mixture is produced?

A nice way to express a form of the Markownikoff (sp) rule:smile: