The Student Room Group

Isomerism

Does cis trans isomerism occur in Ring structure (cyclic compound) ?
Reply 1
Why does this compound show cis trans isomerism?
Reply 2
Yes, isomerism can occur in cyclic structures, just look for chirality (an atom with 4 different groups attached to it).

If you look at the carbons that each H and Br atom is attached to in that image, you should realise they're chiral (it has 4 different groups). This means that it has 2 unique combinations in which those 4 groups can be arranged to be structurally distinct from one another. When both Bromines are facing towards you is one isomer, and when both bromines are facing opposite from each other (if both bromines faced away, it would be the same structure as them both facing us, just flipped around). These two isomers are in that image.

The consequences of this can be seen in regioselectivity/stereoselectivity of reactions, i.e. Br is more bulky than H, so expect nucleophiles to attack from the H-side rather than Br
Reply 3
Original post by Dylann
Yes, isomerism can occur in cyclic structures, just look for chirality (an atom with 4 different groups attached to it).

If you look at the carbons that each H and Br atom is attached to in that image, you should realise they're chiral (it has 4 different groups). This means that it has 2 unique combinations in which those 4 groups can be arranged to be structurally distinct from one another. When both Bromines are facing towards you is one isomer, and when both bromines are facing opposite from each other (if both bromines faced away, it would be the same structure as them both facing us, just flipped around). These two isomers are in that image.

The consequences of this can be seen in regioselectivity/stereoselectivity of reactions, i.e. Br is more bulky than H, so expect nucleophiles to attack from the H-side rather than Br

Yes, Chiral carbon is seen. But wanted to ask about cis trans.
It would be great if you could tell how cis trans is present.
Thank you so much :smile:
Reply 4
Original post by googie3
Yes, Chiral carbon is seen. But wanted to ask about cis trans.
It would be great if you could tell how cis trans is present.
Thank you so much :smile:


The molecule with bromines on the same side is cis (same), the molecule with the bromines opposite is trans
Reply 5
Does this molecule show cis trans at the point where we see chirality?
Reply 6
Original post by Dylann
The molecule with bromines on the same side is cis (same), the molecule with the bromines opposite is trans

I shared another compound's structure. Please explain the stereoisomerism shown.

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