[johnboy88]

Hello

Am I right in saying that there is only one possible product (aside from HCl) when cyclopentane reacts with chlorine? If only one hydrogen is replaced by one chlorine, then there can be no stereoisomers right? Any other isomers, e.g. pentene would require the breaking of carbon bonds?

Could someone confirm or correct me here?

Many thanks

[Dan]

Am I right in saying that there is only one possible product (aside from HCl) when cyclopentane reacts with chlorine?

No, there will be a mess of products.

If only one hydrogen is replaced by one chlorine, then there can be no stereoisomers right?

Correct

Any other isomers, e.g. pentene would require the breaking of carbon bonds?

Pentene is not an isomer of chlorocyclopentane. Isomers have the same constitution (formula).

[johnboy88]

Thank you for your response.

When i said pentene, i meant chloropentene sorry.

You say a mess of products, would this involve introducing methyl groups and reducing the number of carbons in the ring?

[discodermolide]

Thank you for your response.

When i said pentene, i meant chloropentene sorry.

You say a mess of products, would this involve introducing methyl groups and reducing the number of carbons in the ring?

You will not introduce any methyl groups, reacting with HCl that is not possible.You will also not get any chloropentene, that would mean breaking a C-C.
What Dan meant is the you will probably get every possible combination of chlorinated products, di-tri- chlorination etc up to pentachlorination. Even double chlorination is possible. This is a mess of products.

[johnboy88]

Sorry if i am making a mistake here but just to clarify it is cl2 that is reacting with cyclopentane and not HCl. My objective is to draw the structural formula for the possible products when these two react. The other product, HCl, is ignored.

If only one hydrogen is replaced with a chlorine, i am confused at the possible range of chlorinated products there could be.

Many thanks for your replies.

[Dan]

If only one hydrogen is replaced with a chlorine, i am confused at the possible range of chlorinated products there could be.

If only one hydrogen is substituted for Cl, then yes, there is only one product.

However, the point we're making is that you will get a distribution of products in which between 1 and (theoretically) 10 chlorine atoms have been incorporated on the cyclopentane ring. Some of these products are less likely to form than others, but controlling the product distribution is extremely difficult in these types of reactions. You would certainly expect to see di- and trisubstitution as significant components of the reaction mixture at the end.