Give the structure of each of the following aromatic hydrocarbons. $$ \begin{array}{ll}{\text { a. } o \text { -ethyltoluene }} & {\text { c. } m \text { -diethylbenzene }} \\ {\text { b. } p \text { -di-tert-butylbenzene }} & {\text { d. } 1 \text { -phenyl-2-butene }}\end{array} $$

Short Answer

Expert verified
a. o-ethyltoluene: $$ \begin{array}{c} \mathrm{CH}_{3} \\ | \\ \mathrm{C}_{2} \mathrm{H}_{5} - \mathrm{C}_{1} - \mathrm{C}_{6} \mathrm{H}_{4} - \mathrm{C}_{2} \\ | \\ \mathrm{CH}_{3} \end{array} $$ b. p-di-tert-butylbenzene: $$ \mathrm{C}(\mathrm{CH}_{3})_{3} - \mathrm{C}_{1} - \mathrm{C}_{6} \mathrm{H}_{4} - \mathrm{C}_{4} - \mathrm{C}(\mathrm{CH}_{3})_{3} $$ c. m-diethylbenzene: $$ \mathrm{C}_{2} \mathrm{H}_{5} - \mathrm{C}_{1} - \mathrm{C}_{6} \mathrm{H}_{4} - \mathrm{C}_{3} - \mathrm{C}_{2} \mathrm{H}_{5} $$ d. 1-phenyl-2-butene: $$ \mathrm{C}_{1} - \mathrm{C}_{6} \mathrm{H}_{5} - \mathrm{C}_{2} = \mathrm{CH} - \mathrm{CH}_{3} $$

Step by step solution

01

Draw the basic benzene ring

Start by drawing a hexagon to represent the six carbon atoms that form the backbone of the aromatic hydrocarbon. Place three alternating double bonds and three single bonds along the edges of the hexagon.
02

Add the substituents to the benzene ring

For each of the compounds, we will add the substituents (carbon chains) to the benzene ring according to the given name of the hydrocarbon. a. o-ethyltoluene: "o" stands for "ortho" which means that the two substituents are on adjacent carbon atoms. In this case, we have an ethyl group (-C2H5) and a methyl group (-CH3) since toluene is a benzene ring with a methyl group attached. Attach these groups to the benzene ring on adjacent carbon atoms. b. p-di-tert-butylbenzene: "p" stands for "para" which means that the two substituents are on opposite sides of the benzene ring. Here, we have two tert-butyl groups (-C(CH3)3). Place these groups on opposite carbon atoms in the benzene ring. c. m-diethylbenzene: "m" stands for "meta" which means that the two substituents are separated by one carbon atom. In this case, we have two ethyl groups (-C2H5). Attach these groups to the benzene ring with one carbon atom in between. d. 1-phenyl-2-butene: This molecule consists of a benzene ring attached to a 4-carbon chain with a double bond between the second and third carbon. First, draw a 4-carbon chain with a double bond between the second and third carbon. Next, attach the benzene ring to the first carbon atom of the chain.
03

Draw final structures

a. o-ethyltoluene: CH3 | C2H5-C1-C6H4-C2 | CH3 b. p-di-tert-butylbenzene: C(CH3)3-C1-C6H4-C4-C(CH3)3 c. m-diethylbenzene: C2H5-C1-C6H4-C3-C2H5 d. 1-phenyl-2-butene: C1-C6H5-C2=CH-CH3

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Most popular questions from this chapter

Ethylene oxide is an important industrial chemical. Although most ethers are unreactive, ethylene oxide is quite reactive. It resembles $\mathrm{C}_{2} \mathrm{H}_{4}$ in its reactions in that addition reactions occur across the \(\mathrm{C}-\mathrm{O}\) bond in ethylene oxide. a. Why is ethylene oxide so reactive? (Hint: Consider the bond angles in ethylene oxide as compared with those predicted by the VSEPR model.) b. Ethylene oxide undergoes addition polymerization, forming a polymer used in many applications requiring a nonionic surfactant. Draw the structure of this polymer.

Consider the reaction of propane with chlorine (and appropriate catalyst). a. How many different monochloro products are possible? Name them. b. How many different dichloro products are possible? Name them.

Draw all the structural and geometrical (cis–trans) isomers of bromochloropropene.

Reagents such as \(\mathrm{HCl}\) , HBr, and $\mathrm{HOH}\left(\mathrm{H}_{2} \mathrm{O}\right)$ can add across carbon-carbon double and triple bonds, with \(\mathrm{H}\) forming a bond to one of the carbon atoms in the multiple bond and \(\mathrm{Cl}\) , Br, or OH forming a bond to the other carbon atom in the multiple bond. In some cases, two products are possible. For the major organic product, the addition occurs so that the hydrogen atom in the reagent attaches to the carbon atom in the multiple bond that already has the greater number of hydrogen atoms bonded to it. With this rule in mind, draw the structure of the major product in each of the following reactions.

If one hydrogen in a hydrocarbon is replaced by a halogen atom, the number of isomers that exist for the substituted compound depends on the number of types of hydrogen in the original hydrocarbon. Thus there is only one form of chloroethane (all hydrogens in ethane are equivalent), but there are two isomers of propane that arise from the substitution of a methyl hydrogen or a methylene hydrogen. How many isomers can be obtained when one hydrogen in each of the compounds named below is replaced by a chlorine atom? $$ \begin{array}{ll}{\text { a. } n \text { -pentane }} & {\text { c. } 2,4 \text { -dimethylpentane }} \\ {\text { b. } 2 \text { -methylbutane }} & {\text { d. methylcyclobutane }}\end{array} $$

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