Chapter 10

Write equations for the following reactions, representing the reactants and products using structural formulas. (a) The reaction of acetic acid and sodium hydroxide (b) The reaction of methylamine with \(\mathrm{HCl}\)

Write an equation for the formation of the following polymers. (a) Polystyrene, from styrene \(\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}=\mathrm{CH}_{2}\right)\) (b) PET (polyethylene terephthalate), from ethylene glycol and terephthalic acid

Write equations for the following reactions, representing the reactants and products using structural formulas. (a) The hydrolysis of the amide \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CONHCH}_{3}\) to form benzoic acid and methylamine (b) The hydrolysis of \(+\mathrm{CO}\left(\mathrm{CH}_{2}\right)_{4} \mathrm{CONH}\left(\mathrm{CH}_{2}\right)_{6} \mathrm{NH} \rightarrow_{n}\) (nylon-6,6, a polyamide) to give a carboxylic acid and an amine

Draw the structure of each of the following compounds: (a) 2,2 -dimethylpentane (b) 3,3 -diethylpentane (c) 3 -ethyl-2-methylpentane (d) 3 -ethylhexane

A Structural isomers. (a) Draw all of the isomers possible for \(\mathrm{C}_{3} \mathrm{H}_{8} \mathrm{O}\). Give the systematic name of each, and tell into which class of compound it fits. (b) Draw the structural formulas for an aldehyde and a ketone with the molecular formula \(\mathrm{C}_{4} \mathrm{H}_{8} \mathrm{O}\). Give the systematic name of each.

A Draw structural formulas for possible isomers of the dichlorinated propane, \(\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{Cl}_{2}\). Name each compound.

Draw structural formulas for possible isomers with the formula \(\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{ClBr}\), and name each isomer.

Give structural formulas and systematic names for the three structural isomers of trimethylbenzene, \(\mathrm{C}_{6} \mathrm{H}_{3}\left(\mathrm{CH}_{3}\right)_{3}\)

Give structural formulas and systematic names for possible isomers of dichlorobenzene, \(\mathrm{C}_{6} \mathrm{H}_{4} \mathrm{Cl}_{2}\)

Benzoic acid occurs in many berries. When humans eat berries, benzoic acid is converted to hippuric acid in the body by reaction with the amino acid glycine \(\mathrm{H}_{2} \mathrm{NCH}_{2} \mathrm{CO}_{2} \mathrm{H} .\) Draw the structure of hippuric acid, knowing it is an amide formed by reaction of the carboxylic acid group of benzoic acid and the amino group of glycine. Why is hippuric acid referred to as an acid?

Consider the reaction of cis-2-butene with \(\mathrm{H}_{2}\) (in the presence of a catalyst). (a) Draw the structure, and give the name of the reaction product. Is this reaction product chiral? (b) Draw an isomer of the reaction product.

Draw the structure of glyceryl trilaurate, a fat. Lauric acid (page 489) has the formula \(\mathrm{C}_{11} \mathrm{H}_{23} \mathrm{CO}_{2} \mathrm{H}\) (a) Write an equation for the saponification of glyceryl trilaurate. (b) Write an equation for the reaction that could be used to prepare biodiesel fuel from this fat.

A well-known company selling outdoor clothing has recently introduced jackets made of recycled polyethylene terephthalate (PET), the principal material in many soft drink bottles. Another company makes PET fibers by treating recycled bottles with methanol to give the diester dimethyl terephthalate and ethylene glycol and then repolymerizes these compounds to give new PET. Write a chemical equation to show how the reaction of PET with methanol can give dimethyl terephthalate and ethylene glycol.

Identify the reaction products, and write an equation for the following reactions of \(\mathrm{CH}_{2}=\mathrm{CHCH}_{2} \mathrm{OH}\). (a) \(\mathrm{H}_{2}\) (hydrogenation, in the presence of a catalyst) (b) Oxidation (excess oxidizing agent) (c) Addition polymerization (d) Ester formation, using acetic acid

Write a chemical equation describing the reaction between glycerol and stearic acid (Table 10.9 ) to give glyceryl tristearate.

The product of an addition reaction of an alkene is often predicted by Markovnikov's rule. (a) Draw the structure of the product of adding HBr to propene, and give the name of the product. (b) Draw the structure and give the name of the compound that results from adding \(\mathrm{H}_{2} \mathrm{O}\) to 2 -methyl1-butene. (c) If you add \(\mathrm{H}_{2} \mathrm{O}\) to 2 -methyl-2-butene, is the product the same or different than the product from the reaction in part (b)?

An unknown colorless liquid has the formula \(\mathrm{C}_{4} \mathrm{H}_{10} \mathrm{O}\) Draw the structures for the four alcohol compounds that have this formula.

Which of the following compounds produces acetic acid when treated with an oxidizing agent such as \(\mathrm{KMnO}_{4} ?\) EQUATION CANT COPY

Aydrolysis of an unknown ester of butanoic acid, \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{R},\) produces an alcohol \(\mathrm{A}\) and buta- noic acid. Oxidation of this alcohol forms an acid \(\mathrm{B}\) that is a structural isomer of butanoic acid. Give the names and structures for alcohol \(\mathrm{A}\) and acid \(\mathrm{B}\).

You are asked to identify an unknown colorless, liquid carbonyl compound. Analysis has determined that the formula for this unknown is \(\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{O} .\) Only two compounds match this formula. (a) Draw structures for the two possible compounds. (b) To decide which of the two structures is correct, you react the compound with an oxidizing agent and isolate from that reaction a compound that is found to give an acidic solution in water. Use this result to identify the structure of the unknown. (c) Name the acid formed by oxidation of the unknown.

Describe a simple chemical test to tell the difference between \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CH}_{2}\) and its isomer cyclopentane.

Describe a simple chemical test to tell the difference between 2 -propanol and its isomer methyl ethyl ether.

A An unknown ester has the formula \(\mathrm{C}_{4} \mathrm{H}_{8} \mathrm{O}_{2}\) Hydrolysis gives methanol as one product. Identify the ester, and write an equation for the hydrolysis reaction.

A Addition of water to alkene X gives an alcohol Y. Oxidation of Y produces 3,3 -dimethyl-2-pentanone. Identify \(\mathrm{X}\) and \(\mathrm{Y}\), and write equations for the two reactions.

Carbon atoms appear in organic compounds in several different ways with single, double, and triple bonds combining to give an octet configuration. Describe the various ways that carbon can bond to reach an octet, and give the name and draw the structure of a compound that illustrates that mode of bonding.

What important properties do the following characteristics impart to a polymer? (a) Cross-linking in polyethylene (b) The OH groups in polyvinyl alcohol (c) Hydrogen bonding in a polyamide like nylon

Maleic acid is prepared by the catalytic oxidation of benzene. It is a dicarboxylic acid; that is, it has two carboxylic acid groups. (a) Combustion of \(0.125 \mathrm{g}\) of the acid gives \(0.190 \mathrm{g}\) of \(\mathrm{CO}_{2}\) and \(0.0388 \mathrm{g}\) of \(\mathrm{H}_{2} \mathrm{O} .\) Calculate the empirical formula of the acid. (b) A 0.261 -g sample of the acid requires 34.60 mL of \(0.130 \mathrm{M} \mathrm{NaOH}\) for complete titration (so that the H ions from both carboxylic acid groups are used). What is the molecular formula of the acid? (c) Draw a Lewis structure for the acid. (d) Describe the hybridization used by the C atoms. (e) What are the bond angles around each \(C\) atom?