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Ch.3 - Chemical Reactions and Reaction Stoichiometry
Chapter 3, Problem 56b

(b) Nicotine, a component of tobacco, is composed of C, H, and N. A 5.250-mg sample of nicotine was combusted, producing 14.242 mg of CO2 and 4.083 mg of H2O. What is the empirical formula for nicotine? If nicotine has a molar mass of 160 ± 5 g/mol, what is its molecular formula?

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1
Determine the moles of carbon in CO<sub>2</sub> and the moles of hydrogen in H<sub>2</sub>O. Use the molar mass of CO<sub>2</sub> (44.01 g/mol) and H<sub>2</sub>O (18.02 g/mol) to convert the mass of CO<sub>2</sub> and H<sub>2</sub>O to moles. Remember that each mole of CO<sub>2</sub> contains one mole of carbon and each mole of H<sub>2</sub>O contains two moles of hydrogen.
Calculate the mass of carbon and hydrogen in the sample by multiplying the moles of carbon and hydrogen by their respective atomic masses (12.01 g/mol for C and 1.008 g/mol for H).
Subtract the total mass of carbon and hydrogen from the initial mass of the nicotine sample to find the mass of nitrogen. Use the atomic mass of nitrogen (14.01 g/mol) to convert this mass to moles of nitrogen.
Find the simplest whole number ratio of moles of C, H, and N to determine the empirical formula. Divide the moles of each element by the smallest number of moles calculated among C, H, and N.
To find the molecular formula, divide the molar mass of nicotine (given as 160 ± 5 g/mol) by the molar mass of the empirical formula unit. Multiply the subscripts in the empirical formula by this ratio to get the molecular formula.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Combustion Analysis

Combustion analysis is a technique used to determine the elemental composition of organic compounds. In this process, a sample is burned in excess oxygen, producing carbon dioxide (CO2) and water (H2O). The masses of these products are measured to calculate the amounts of carbon, hydrogen, and other elements in the original sample, which is essential for determining the empirical formula.
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Combustion of Non-Hydrocarbons

Empirical Formula

The empirical formula represents the simplest whole-number ratio of atoms of each element in a compound. It is derived from the moles of each element calculated from the combustion products. For nicotine, the empirical formula can be determined by converting the masses of CO2 and H2O produced into moles of carbon and hydrogen, and then finding the ratio of these moles to establish the formula.
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Empirical vs Molecular Formula

Molecular Formula

The molecular formula indicates the actual number of atoms of each element in a molecule of a compound. It can be derived from the empirical formula by comparing the molar mass of the compound to the molar mass of the empirical formula. If the molar mass of nicotine is known, the molecular formula can be calculated by determining how many times the empirical formula fits into the molar mass.
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Related Practice
Textbook Question

(a) Combustion analysis of toluene, a common organic solvent, gives 5.86 mg of CO2 and 1.37 mg of H2O. If the compound contains only carbon and hydrogen, what is its empirical formula?

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Textbook Question

(b) Menthol, the substance we can smell in mentholated cough drops, is composed of C, H, and O. A 0.1005-g sample of menthol is combusted, producing 0.2829 g of CO2 and 0.1159 g of H2O. What is the empirical formula for menthol? If menthol has a molar mass of 156 g/mol, what is its molecular formula?

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Textbook Question

(a) The characteristic odor of pineapple is due to ethyl butyrate, a compound containing carbon, hydrogen, and oxygen. Combustion of 2.78 mg of ethyl butyrate produces 6.32 mg of CO2 and 2.58 mg of H2O. What is the empirical formula of the compound?

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Textbook Question

Valproic acid, used to treat seizures and bipolar disorder, is composed of C, H, and O. A 0.165-g sample is combusted to produce 0.166 g of water and 0.403 g of carbon dioxide. What is the empirical formula for valproic acid?

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Textbook Question

Propenoic acid, C3H4O2, is a reactive organic liquid that is used in the manufacturing of plastics, coatings, and adhesives. An unlabeled container is thought to contain this liquid. A 0.275-g sample of the liquid is combusted to produce 0.102 g of water and 0.374 g carbon dioxide. Is the unknown liquid propenoic acid? Support your reasoning with calculations.

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Textbook Question

Washing soda, a compound used to prepare hard water for washing laundry, is a hydrate, which means that a certain number of water molecules are included in the solid structure. Its formula can be written as Na2CO3 # xH2O, where x is the number of moles of H2O per mole of Na2CO3. When a 2.558-g sample of washing soda is heated at 125 C, all the water of hydration is lost, leaving 0.948 g of Na2CO3. What is the value of x?

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