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Chapter 22: Problem 19

Draw a structural formula for each of the following compounds. a. 2-methylpropane b. 2-methylbutane c. 2-methylpentane d. 2-methylhexane

Short Answer

Expert verified
a. CH3 | CH3-C-CH3 b. CH3 CH3 | | CH3-C-CH2-C-CH3 c. CH3 CH3 | | CH3-C-CH2-C-CH2-C-CH3 d. CH3 CH3 | | CH3-C-CH2-C-CH2-CH2-C-CH3

Step by step solution

01

Identify the longest carbon chain

Using the names given, we can identify the main carbon chain in each compound by looking at their suffixes: propane, butane, pentane, and hexane. These contain 3, 4, 5, and 6 carbon atoms, respectively.
02

Identify the position of the methyl group

In each compound, the prefix "2-methyl" indicates that there is a methyl group (CH3-) attached to the second carbon atom in the main chain.
03

Draw the structural formula for each compound

Now, we will draw the structural formula for each compound using the information from steps 1 and 2. a. 2-methylpropane: Propane has a three-carbon chain, the structure is: CH3 | CH3-C-CH3 b. 2-methylbutane: Butane has a four-carbon chain. The structure is: CH3 CH3 | | CH3-C-CH2-C-CH3 c. 2-methylpentane: Pentane has a five-carbon chain. The structure is: CH3 CH3 | | CH3-C-CH2-C-CH2-C-CH3 d. 2-methylhexane: Hexane has a six-carbon chain. The structure is: CH3 CH3 | | CH3-C-CH2-C-CH2-CH2-C-CH3

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Structural Formula
In Organic Chemistry, a structural formula is a way to represent molecules by showing how atoms are connected to each other through chemical bonds. Unlike simple molecular formulas, which only display the number and type of atoms, structural formulas give us a visual depiction of the molecule's geometry. This representation can be crucial when trying to understand the properties and behavior of a compound.
For example:
  • The structural formula of ethanol is represented as CH3CH2OH. It clearly shows the arrangement of carbon, hydrogen, and oxygen atoms.
  • Simple line representations might use dashes to show bonds, whereas more detailed ball-and-stick models give a three-dimensional view.
  • Structural formulas help in visualizing branches in complex molecules like those in the exercise, where a methyl group (CH3) is attached to a carbon chain.
Understanding structural formulas is vital for identifying how molecules might interact in reactions or biological processes.
Alkanes
Alkanes are a key class of hydrocarbons in organic chemistry. These compounds contain only carbon and hydrogen atoms. They are also known as saturated hydrocarbons because they have single bonds between carbon atoms. Alkanes can be straight chains or branched chains.
Here's a simple way to grasp the concept of alkanes:
  • The general formula for an alkane is CnH2n+2, where n is the number of carbon atoms.
  • In alkanes, each carbon atom forms four single covalent bonds with other atoms. Typically, this leads to a zig-zag or linear structure.
  • Examples include methane (CH4), ethane (C2H6), and propane (C3H8).
Alkanes are typically not very reactive due to their strong C-C and C-H bonds, but they play a significant role as fuels鈥攆or instance, propane is used in home heating. Identifying the parent alkane chain is crucial before further modification or branching, as shown in the exercises.
Methyl Groups
A methyl group is a chemical group derived from methane (CH4) by the removal of one hydrogen atom, resulting in CH3-. When a methyl group is connected to a carbon chain, it acts as a branch, changing the properties and name of the parent alkane. This is how branched alkanes form.
To understand the importance of methyl groups in organic chemistry, consider:
  • Methyl groups are named as substituents in the IUPAC nomenclature when not part of the main carbon chain.
  • They can be found attached to various positions on a carbon chain, significantly affecting the compound's structure and properties.
  • In the case of the exercise examples, the methyl group is appended at the second carbon of the main chain.
Recognizing where and how methyl groups attach is essential for drawing structural formulas accurately. Their presence can alter boiling points, densities, and even the reactivity of compounds.

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Most popular questions from this chapter

For each of the following, fill in the blank with the correct response. All of these fill-in-the-blank problems pertain to material covered in the sections on alkanes, alkenes and alkynes, aromatic hydrocarbons, and hydrocarbon derivatives. a. The first 鈥渙rganic鈥� compound to be synthesized in the laboratory, rather than being isolated from nature, was , which was prepared from . b. An organic compound whose carbon鈥揷arbon bonds are all single bonds is said to be . c. The general orientation of the four pairs of electrons around the carbon atoms in alkanes is . d. Alkanes in which the carbon atoms form a single unbranched chain are said to be alkanes. e. Structural isomerism occurs when two molecules have the same number of each type of atom but exhibit different arrangements of the between those atoms. f. The systematic names of all saturated hydrocarbons have the ending added to a root name that indicates the number of carbon atoms in the molecule. g. For a branched hydrocarbon, the root name for the hydrocarbon comes from the number of carbon atoms in the continuous chain in the molecule. h. The positions of substituents along the hydrocarbon framework of a molecule are indicated by the of the carbon atom to which the substituents are attached. i. The major use of alkanes has been in reactions, as a source of heat and light. j. With very reactive agents, such as the halogen elements, alkanes undergo reactions, whereby a new atom replaces one or more hydrogen atoms of the alkane. k. Alkenes and alkynes are characterized by their ability to undergo rapid, complete reactions, by which other atoms attach themselves to the carbon atoms of the double or triple bond. l. Unsaturated fats may be converted to saturated fats by the process of . m. Benzene is the parent member of the group of hydrocarbons called hydrocarbons. n. An atom or group of atoms that imparts new and characteristic properties to an organic molecule is called a group. o. A alcohol is one in which there is only one hydrocarbon group attached to the carbon atom holding the hydroxyl group. p. The simplest alcohol, methanol, is prepared industrially by the hydrogenation of . q. Ethanol is commonly prepared by the of certain sugars by yeast. r. Both aldehydes and ketones contain the group, but they differ in where this group occurs along the hydrocarbon chain. s. Aldehydes and ketones can be prepared by of the corresponding alcohol. t. Organic acids, which contain the group, are typically weak acids. u. The typically sweet-smelling compounds called result from the condensation reaction of an organic acid with an .

Helicenes are extended fused polyaromatic hydrocarbons that have a helical or screw-shaped structure. a. A \(0.1450-\) g sample of solid helicene is combusted in air to give 0.5063 \(\mathrm{g} \mathrm{CO}_{2}\) . What is the empirical formula of this helicene? b. If a 0.0938 -g sample of this helicene is dissolved in 12.5 g of solvent to give a 0.0175 M solution, what is the molecular formula of this helicene? c. What is the balanced reaction for the combustion of this helicene?

A common shorthand notation to draw organic structures is to use lines to represent \(\mathrm{C}-\mathrm{C}\) bonds. For example, the short- hand notation for the two structural isomers of the formula \(\mathrm{C}_{4} \mathrm{H}_{10}\) are: At the end of each zigzag line is a carbon atom. The \(\mathrm{C}-\mathrm{H}\) bonds are omitted in such shorthand notation. Use line notation to illustrate the structural isomers of \(\mathrm{C}_{6} \mathrm{H}_{14}\)

A chemical 鈥渂reathalyzer鈥� test works because ethanol in the breath is oxidized by the dichromate ion (orange) to form acetic acid and chromium(III) ion (green). The balanced reaction is You analyze a breathalyzer test in which 4.2 \(\mathrm{mg} \mathrm{K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7}\) was reduced. Assuming the volume of the breath was 0.500 \(\mathrm{L}\) at \(30 .^{\circ} \mathrm{C}\) and \(750 . \mathrm{mm}\) Hg, what was the mole percent alcohol of the breath?

Poly(lauryl methacrylate) is used as an additive in motor oils to counter the loss of viscosity at high temperature. The structure is The long hydrocarbon chain of poly(lauryl methacrylate) makes the polymer soluble in oil (a mixture of hydrocarbons with mostly 12 or more carbon atoms). At low temperatures the polymer is coiled into balls. At higher temperatures the balls uncoil and the polymer exists as long chains. Explain how this helps control the viscosity of oil.
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