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Chapter 22: Problem 18

Draw a structural formula for each of the following compounds. a. 2,2 -dimethylheptane c. 3,3 -dimethylheptane b. 2,3 -dimethylheptane d. 2,4 -dimethylheptane

Short Answer

Expert verified
The structural formulas for the given dimethylheptane isomers are: a. 2,2-dimethylheptane: \( \displaystyle \begin{array}{ccccc} & C\! & & & \\ -C\! & -C\! & -C\! & -C\! & -C\! & -C\! & -C \end{array} \) c. 3,3-dimethylheptane: \( \displaystyle \begin{array}{ccccc} & & C\! & \\ -C\! & -C\! & -C\! & -C\! & -C\! & -C\! & -C \end{array} \) b. 2,3-dimethylheptane: \( \displaystyle \begin{array}{ccccc} & C\! \\ -C\! & -C\! & -C\! & -C\! & -C\! & -C\! & -C \\ & & C \end{array} \) d. 2,4-dimethylheptane: \( \displaystyle \begin{array}{ccccc} & C\! & \\ -C\! & -C\! & -C\! & -C\! & -C\! & -C\! & -C \\ & & & C \end{array} \)

Step by step solution

01

Identify the parent chain

The parent chain in each compound is heptane, which has 7 carbon atoms in a straight chain. In all four compounds, we will start by drawing the heptane chain.
02

Add the substituents

The substituents in these compounds are methyl groups (CH3). The number in the compound name represents the position of the methyl group on the heptane chain. We will draw the methyl groups at the indicated positions for each compound. a. 2,2 -dimethylheptane Draw the heptane chain: \( \displaystyle \begin{array}{cc} \text{C}\ -\ C\ -\ C\ -\ C\ -\ C\ -\ C\ -\ C \end{array} \) Add two methyl groups at position 2: \( \displaystyle \begin{array}{ccccc} & C\! & & & \\ -C\! & -C\! & -C\! & -C\! & -C\! & -C\! & -C \end{array} \) c. 3,3 -dimethylheptane Draw the heptane chain: \( \displaystyle \begin{array}{cc} \text{C}\ -\ C\ -\ C\ -\ C\ -\ C\ -\ C\ -\ C \end{array} \) Add two methyl groups at position 3: \( \displaystyle \begin{array}{ccccc} & & C\! & \\ -C\! & -C\! & -C\! & -C\! & -C\! & -C\! & -C \end{array} \) b. 2,3 -dimethylheptane Draw the heptane chain: \( \displaystyle \begin{array}{cc} \text{C}\ -\ C\ -\ C\ -\ C\ -\ C\ -\ C\ -\ C \end{array} \) Add one methyl group at position 2 and one at position 3: \( \displaystyle \begin{array}{ccccc} & C\! \\ -C\! & -C\! & -C\! & -C\! & -C\! & -C\! & -C \\ & & C \end{array} \) d. 2,4 -dimethylheptane Draw the heptane chain: \( \displaystyle \begin{array}{cc} \text{C}\ -\ C\ -\ C\ -\ C\ -\ C\ -\ C\ -\ C \end{array} \) Add one methyl group at position 2 and one at position 4: \( \displaystyle \begin{array}{ccccc} & C\! & \\ -C\! & -C\! & -C\! & -C\! & -C\! & -C\! & -C \\ & & & C \end{array} \)

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Most popular questions from this chapter

How would you synthesize each of the following? a. 1,2 -dibromopropane from propene b. acetone (2-propanone) from an alcohol c. tert-butyl alcohol (2-methyl-2-propanol) from an alkene (See Exercise 62.) d. propanoic acid from an alcohol

Which of the noncyclic isomers of bromochloropropene are optically active?

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 "organic" compound to be synthesized in the laboratory, rather than being isolated from nature, was ____ ,which was prepared from _______. b. An organic compound whose carbon-carbon 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 but they differ in where this group occurs along the hvdrocarbon 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 ________.

Isoprene is the repeating unit in natural rubber. The structure of isoprene is a. Give a systematic name for isoprene. b. When isoprene is polymerized, two polymers of the form are possible. In natural rubber, the cis configuration is found. The polymer with the trans configuration about the double bond is called gutta percha and was once used in the manufacture of golf balls. Draw the structure of natural rubber and gutta percha showing three repeating units and the configuration about the carbon-carbon double bonds.

For the following formulas, what types of isomerism could be exhibited? For each formula, give an example that illustrates the specific type of isomerism. The types of isomerism are structural, geometric, and optical. a. \(\mathrm{C}_{6} \mathrm{H}_{12}\) b. \(\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O}\) c. \(\mathrm{C}_{6} \mathrm{H}_{4} \mathrm{Br}_{2}\)
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