Question

Draw a structural formula for the cycloalkene with the molecular formula \(\mathrm{C}_{6} \mathrm{H}_{10}\) that reacts with \(\mathrm{Cl}_{2}\) to give each compound. (a) Cl[C]1CCCC[C]1Cl (b) CC1CC(Cl)C(Cl)C1 (c) CC1(Cl)CCCC1Cl (d) ClCC1(Cl)CCCC1

Short answer

Based on the analysis and solution, the structural formula for the cycloalkene with the molecular formula \(\mathrm{C}_{6} \mathrm{H}_{10}\) that reacts with \(\mathrm{Cl}_{2}\) to form the given compounds is cyclohexene: C1C=CCCC1 Cyclohexene has the molecular formula \(\mathrm{C}_{6} \mathrm{H}_{10}\) and contains a double bond in the ring. Upon reacting with \(\mathrm{Cl}_{2}\), it forms the given product structures by replacing the double bond with two attached chlorine atoms.

Step-by-step solution

Analyze given structures

The exercise gives us four product structures: (a) Cl[C]1CCCC[C]1Cl (b) CC1CC(Cl)C(Cl)C1 (c) CC1(Cl)CCCC1Cl (d) ClCC1(Cl)CCCC1 These structures all have a six-membered ring with at least one double bond and two chlorine atoms attached to the carbon atoms.

Determine possible cycloalkene structure

The molecular formula given is \(\mathrm{C}_{6} \mathrm{H}_{10}\). As we can see, the structures given have six carbon atoms in a ring structure and we know there must be a double bond in the ring, which gives a cycloalkene structure. We can write the structure of cyclohexene as: C1C=CCCC1 Cyclohexene has the molecular formula \(\mathrm{C}_{6} \mathrm{H}_{10}\), and it contains a double bond.

Predict the reaction, bicyclooctene with \(\mathrm{Cl}_{2}\)

Now we will verify if cyclohexene reacts with \(\mathrm{Cl}_{2}\) to form the given structures: The reaction between cyclohexene and \(\mathrm{Cl}_{2}\) can be written as follows: C1C=CCCC1 + ClCl -> Product During this reaction, the double bond in the ring reacts with the chlorine molecule, and two chlorine atoms attach to the carbon atoms, replacing the double bond.

Verify formation

Now let's check if the given structures can be formed by the addition of chlorine: (a) Cyclohexene(Cl-1,3) - This structure has two chlorine atoms attached to the first and third carbon of the ring. (b) Cyclohexene(Cl-1,2) - This structure has two chlorine atoms attached to the first and second carbon of the ring. (c) Cyclohexene(Cl-2,5) - This structure has two chlorine atoms attached to the second and fifth carbon of the ring. (d) Cyclohexene(Cl-2,3) - This structure has two chlorine atoms attached to the second and third carbon of the ring. Thus, we can conclude that the cyclohexene reacts with \(\mathrm{Cl}_{2}\), and the given structures can be formed by this reaction.