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Question 57

17 mg of a hydrocarbon (M.F. C$$_{10}$$H$$_{16}$$) takes up 8.40 mL of the H$$_2$$ gas measured at 0°C and 760 mm of Hg. Ozonolysis of the same hydrocarbon yields

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The number of double bond/s present in the hydrocarbon is


Correct Answer: 3

The amount of hydrogen consumed during hydrogenation can be used to determine the number of double bonds present in the hydrocarbon.

At STP, one mole of a gas occupies (22{,}400\ \text{mL}). Therefore, the number of moles of hydrogen used is

$$n_{H_2}=\frac{8.40}{22400}=3.75\times10^{-4}\ \text{mol}.$$

The molar mass of (C_{10}H_{16}) is

$$M=(10\times12)+(16\times1)=136\ \text{g mol}^{-1}.$$

Hence, the number of moles of hydrocarbon present is

$$n_{\text{hydrocarbon}}=\frac{0.017}{136}=1.25\times10^{-4}\ \text{mol}.$$

The number of moles of hydrogen consumed per mole of hydrocarbon is

$$\frac{n_{H_2}}{n_{\text{hydrocarbon}}}=\frac{3.75\times10^{-4}}{1.25\times10^{-4}}=3.$$

Since each mole of hydrogen saturates one double bond, the hydrocarbon contains

$$\boxed{3\ \text{double bonds}}.$$

This result is also consistent with the ozonolysis products obtained—acetone, two molecules of formaldehyde, and succinaldehyde—which collectively indicate the presence of three carbon-carbon double bonds in the original molecule.

Therefore, the hydrocarbon contains

$$\boxed{3\ \text{double bonds}}.$$

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