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Organics AS MCQ

Here is the question

Structural and stereoisomerism should be considered when answering this question.
When trans-pent-2-ene reacts with HBr, how many different products can form?
A 1 B 2 C 3 D 4

I thought the answer would be B, because it will form 2 Bromopentane and 3 Bromopentane.
the mark scheme says that the answer is C
does anyone know why?
thanks
Original post by limeferarri
Here is the question

Structural and stereoisomerism should be considered when answering this question.
When trans-pent-2-ene reacts with HBr, how many different products can form?
A 1 B 2 C 3 D 4

I thought the answer would be B, because it will form 2 Bromopentane and 3 Bromopentane.
the mark scheme says that the answer is C
does anyone know why?
thanks

The Q says "stereoisomers" should be considered when answering
..that's the clue
..can either of the two products (you correctly said will form) exist as 2 stereoisomers?
Original post by Davies Chemistry
The Q says "stereoisomers" should be considered when answering
..that's the clue
..can either of the two products (you correctly said will form) exist as 2 stereoisomers?

I thought about cis-trans stereoisomers, but I didn't think about enantiomers. The 2 bromopentane has a chiral carbon, so is that the third isomer?
Original post by limeferarri
I thought about cis-trans stereoisomers, but I didn't think about enantiomers. The 2 bromopentane has a chiral carbon, so is that the third isomer?

That's it!
Reply 4
But 3-bromopentane also has a chiral centre
Original post by whoareu
But 3-bromopentane also has a chiral centre

does it? Draw it out
Reply 6
3-bromopentane doesnt have chiral centre, the third carbon is attached to two same alkyl groups.

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