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Technically yes, since depending on which carbon you start from determines how long it would be. For example, you would want to start on a carbon that is preferably at the "end" of a chain, meaning that you would start counting from a primary carbon (carbon attached to only one carbon).
Yes, when determening the main chain, it does matter which carbon you start with. To expand on Ronald's example, consider a molecule that is seven carbons long if you go directly from left to right, but has a branch of 3 carbons on the 5th carbon. In this case, the chain starting with the branch and stretching to the left will be the main chain as it contains 8 carbons. This is why the length of the main chain is dependent on which carbon you start with.
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