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Ch.23 - Organic and Biological Chemistry
Chapter 23, Problem 144

Isooctane, the substance in gasoline from which the term octane rating derives, has the formula C8H18. Each carbon has four covalent bonds, and the atoms are connected in the sequence shown. Draw the complete structural formula of isooctane.

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Step 1: Understand the molecular formula of isooctane, which is C8H18. This means there are 8 carbon atoms and 18 hydrogen atoms in the molecule.
Step 2: Remember that each carbon atom forms four covalent bonds. This is a fundamental property of carbon due to its four valence electrons.
Step 3: Start drawing the structure by arranging the carbon atoms. Isooctane has a branched structure, with a chain of five carbon atoms and three carbon atoms branching off the second carbon atom in the chain.
Step 4: After arranging the carbon atoms, add the hydrogen atoms. Each carbon atom should be bonded to enough hydrogen atoms such that each carbon atom forms a total of four bonds.
Step 5: Check your structure. Make sure that each carbon atom is forming four bonds (with either carbon or hydrogen), and that you have used all 8 carbon atoms and 18 hydrogen atoms.

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Key Concepts

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

Covalent Bonding

Covalent bonding occurs when two atoms share pairs of electrons, allowing them to achieve a full outer shell and greater stability. In organic compounds like isooctane, carbon atoms typically form four covalent bonds, which can be with other carbon atoms or with hydrogen atoms. This bonding is fundamental to understanding the structure and properties of organic molecules.
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Structural Formula

A structural formula represents the arrangement of atoms within a molecule, showing how atoms are bonded together. It provides more detail than a molecular formula by illustrating the connectivity and spatial orientation of atoms. For isooctane, the structural formula will depict the carbon backbone and the hydrogen atoms attached to each carbon.
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Hydrocarbons

Hydrocarbons are organic compounds composed solely of carbon and hydrogen atoms. They can be classified into aliphatic (straight or branched chains) and aromatic (ring structures) hydrocarbons. Isooctane, being a branched-chain alkane, is an example of a saturated hydrocarbon, where all carbon-carbon bonds are single bonds, contributing to its stability and energy content in fuels.
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Related Practice
Open Question
Fumaric acid is an organic substance widely used as a food additive. Its elemental composition is 41.4% C, 3.5% H, and 55.1% O. A solution made by dissolving 0.1500 g of fumaric acid in water and diluting to a volume of 100.0 mL gave rise to an osmotic pressure of 240.3 mm Hg at 298 K. On titration of a sample weighing 0.573 g, 94.1 mL of 0.105 M NaOH was required to reach an equivalence point. Fumaric acid reacts with 1 mol of H2 to give a hydrogenation product. (a) What is the empirical formula of fumaric acid? (b) What is the molecular weight of fumaric acid? (c) Draw three possible structures for fumaric acid. (d) If fumaric acid contains a trans double bond, which of your structures is correct?
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Textbook Question
Cyclohexane, C6H12, is an important starting material used in the industrial synthesis of nylon. Each carbon has four covalent bonds, two to hydrogen and two to other carbons. Draw the structural formula of cyclohexane.
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Textbook Question
Fructose, C6H12O6, is the sweetest naturally occurring sugar and is found in many fruits and berries. Each carbon has four covalent bonds, each oxygen has two covalent bonds, each hydrogen has one covalent bond, and the atoms are connected in the sequence shown. Draw the complete struc-tural formula of fructose.

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