Chapter 11

What is the name of the straight (unbranched) chain alkane with the formula \(\mathrm{C}_{7} \mathrm{H}_{16} ?\)

What is the molecular formula for an alkane with 12 carbon atoms?

Which of the following is an alkane? Which could be a cycloalkane? (a) \(\mathrm{C}_{2} \mathrm{H}_{4}\) (b) \(\mathrm{C}_{5} \mathrm{H}_{10}\) (c) \(\mathrm{C}_{14} \mathrm{H}_{30}\) (d) \(\mathrm{C}_{7} \mathrm{H}_{8}\)

Isooctane, 2,2,4 -trimethylpentane, is one of the possible structural isomers with the formula \(\mathrm{C}_{8} \mathrm{H}_{18} .\) Draw the structure of this isomer, and draw and name structures of two other isomers of \(\mathrm{C}_{8} \mathrm{H}_{18}\) in which the longest carbon chain is five atoms.

Draw the structure of each of the following compounds: (a) 2,3 -dimethylhexane (b) 2,3 -dimethyloctane (c) 3 -ethylheptane (d) 3 -ethyl-2-methylhexane

Draw structures for 3 -ethylpentane and 2,3 -dimethylpentane.

Draw Lewis structures and name all possible compounds that have a seven-carbon chain with one methyl substituent group. Which of these isomers has a chiral carbon center?

Draw a structure for cycloheptane. Is the seven-member ring planar? Explain your answer.

There are two ethylheptanes (compounds with a sevencarbon chain and one ethyl substituent). Draw the structures and name these compounds. Is either isomer chiral?

Among the 18 structural isomers with the formula \(\mathrm{C}_{8} \mathrm{H}_{18}\) are two with a five-carbon chain having one ethyl and one methyl substituent group. Draw the structures and name these two isomers.

List several typical physical properties of \(\mathrm{C}_{4} \mathrm{H}_{10} .\) Predict the following physical properties of dodecane, \(\mathrm{C}_{12} \mathrm{H}_{26}:\) color, state (s, \(\ell, \mathrm{g}\) ), solubility in water, solubility in a nonpolar solvent.

Write balanced equations for the following reactions of alkanes. (a) the reaction of methane with excess chlorine (b) complete combustion of cyclohexane, \(\mathbf{C}_{6} \mathrm{H}_{12},\) with excess oxygen

Draw structures for the cis and trans isomers of 4-methyl2-hexene.

What structural requirement is necessary for an alkene to have cis and trans isomers? Can cis and trans isomers exist for an alkane? For an alkyne?

A hydrocarbon with the formula \(\mathrm{C}_{5} \mathrm{H}_{10}\) can be either an alkene or a cycloalkane. (a) Draw a structure for each of the possible isomers for \(\mathrm{C}_{5} \mathrm{H}_{10},\) assuming it is an alkene. Six isomers are possible. Give the systematic name of each isomer you have drawn. (b) Draw a structure for a cycloalkane having the formula \(\mathrm{C}_{5} \mathrm{H}_{10}\)

Five alkenes have the formula \(\mathrm{C}_{7} \mathrm{H}_{14}\) and a seven- carbon chain. Draw their structures and name them.

Draw the structure and give the systematic name for the products of the following reactions: (a) \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CH}_{2}+\mathrm{Br}_{2} \longrightarrow\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CHCH}_{3}+\mathrm{H}_{2} \longrightarrow\)

The compound 2,3 -dibromo-2-methylhexane is formed by addition of \(\mathrm{Br}_{2}\) to an alkene. Identify the alkene, and write an equation for this reaction.

Draw structures for alkenes that have the formula \(\mathrm{C}_{3} \mathrm{H}_{5} \mathrm{Cl}\) and name each compound. (In these derivatives of propene, a chlorine atom replaces one hydrogen atom.)

Elemental analysis of a colorless liquid has given its formula as \(\mathrm{C}_{5} \mathrm{H}_{10}\). You recognize that this compound could be either a cycloalkane or an alkene. A chemical test to determine the class to which it belongs involves adding bromine. Explain how this reaction would allow you to distinguish between the two classes.

Draw structural formulas for the following compounds: (a) 1,3 -dichlorobenzene (alternatively called \(m\) dichlorobenzene) (b) 1 -bromo-4-methylbenzene (alternatively called p-bromotoluene)

Write an equation for the preparation of ethylbenzene from benzene and an appropriate compound containing an ethyl group.

Write an equation for the preparation of hexylbenzene from benzene and other appropriate reagents.

A single compound is formed by alkylation of 1,4 -dimethylbenzene. Write the equation for the reaction of this compound with \(\mathrm{CH}_{3} \mathrm{Cl}\) and \(\mathrm{AlCl}_{3}\). What is the structure and name of the product?

Nitration of toluene gives a mixture of two products, one with the nitro group \(\left(-\mathrm{NO}_{2}\right)\) in the ortho position and one with the nitro group in a para position. Draw the structures of the two products.

Draw structural formulas for the following alcohols, and tell whether each is primary, secondary, or tertiary: (a) 1 -butanol (b) 2 -butanol (c) 3,3 -dimethyl-2-butanol (d) 3,3 -dimethyl-1-butanol

Write the formula and draw the structure for each of the following amines: (a) ethylamine (b) dipropylamine (c) butyldimethylamine (d) triethylamine

Name the following amines (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{NH}_{2}\) (b) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{N}\) (c) \(\left(\mathrm{CH}_{3}\right)\left(\mathrm{C}_{2} \mathrm{H}_{5}\right) \mathrm{NH}\) (d) \(\mathrm{C}_{6} \mathrm{H}_{13} \mathrm{NH}_{2}\)

Draw structural formulas for all the alcohols with the formula \(\mathrm{C}_{4} \mathrm{H}_{10} \mathrm{O} .\) Give the systematic name of each.

Draw structural formulas for all the primary amines with the formula \(\mathrm{C}_{4} \mathrm{H}_{9} \mathrm{NH}_{2}\)

Aldehydes and carboxylic acids are formed by oxidation of primary alcohols, and ketones are formed when secondary alcohols are oxidized. Give the name and formula for the alcohol that, when oxidized, gives the following products: (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CHO}\) (b) 2 -hexanone

Draw structural formulas for (a) 2 -pentanone, (b) hexanal, and (c) pentanoic acid.

Draw structural formulas for the following acids and esters: (a) 2-methylhexanoic acid (b) pentyl butanoate (which has the odor of apricots) (c) octyl acetate (which has the odor of oranges)

Give the structural formula and systematic name for the product, if any, from the reactions of each of the following pairs of compounds: (a) pentanal and \(\mathrm{KMnO}_{4}\) (b) pentanal and \(\mathrm{LiAlH}_{4}\) (c) 2-octanone and \(\mathrm{LiAlH}_{4}\) (d) 2 -octanone and \(\mathrm{KMnO}_{4}\)

Give the name and structure of the product of the reaction of benzoic acid and 2 -propanol.

Polyvinyl acetate is the binder in water-based paints. (a) Write an equation for its formation from vinyl acetate. (b) Show a portion of this polymer with three monomer units. (c) Describe how to make polyvinyl alcohol from polyvinyl acetate.

Neoprene (polychloroprene, a kind of rubber) is a polymer formed from the chlorinated butadiene \(\mathrm{H}_{2} \mathrm{C}=\mathrm{CHCCl}=\mathrm{CH}_{2}\) (a) Write an equation showing the formation of polychloroprene from the monomer. (b) Show a portion of this polymer with three monomunits.

Saran is a copolymer of 1,1 -dichloroethene and chloroethene (vinyl chloride). Draw a possible structure for this polymer.

Three different compounds with the formula \(\mathrm{C}_{2} \mathrm{H}_{2} \mathrm{Cl}_{2}\) are known. (a) Two of these compounds are geometric isomers. Draw their structures. (b) The third compound is a structural isomer of the other two. Draw its structure.

Draw the structure of 2 -butanol. Identify the chiral carbon atom in this compound. Draw the mirror image of the structure you first drew. Are the two molecules superimposable?

Draw Lewis structures and name three structural isomers with the formula \(\mathrm{C}_{6} \mathrm{H}_{12} .\) Are any of these isomers chiral?

Draw structures and name the four alkenes that have the formula \(\mathrm{C}_{4} \mathrm{H}_{8}\)

Write equations for the reactions of \(cis-2\)-butene with the following reagents, representing the reactants and products using structural formulas. (a) \(\mathrm{H}_{2} \mathrm{O}\) (b) \(\mathrm{HBr}\) (c) \(\mathrm{Cl}_{2}\)

Draw the structure and name the product formed if the following alcohols are oxidized. Assume that an excess of the oxidizing agent is used. If the alcohol is not expected to react with a chemical oxidizing agent, write NR (no reaction). (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\) (b) 2-butanol (c) 2-methyl-2-propanol (d) 2 -methyl-1-propanol

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 equations for the following reactions, representing the reactants and products using structural formulas. (a) the formation of ethyl acetate from acetic acid and ethanol (b) the hydrolysis of glyceryl tristearate (the triester of glycerol with stearic acid, a fatty acid)

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 nylon-66, \(\left[-\mathrm{CO}\left(\mathrm{CH}_{2}\right)_{4} \mathrm{CONH}\left(\mathrm{CH}_{2}\right)_{6} \mathrm{NH}-\right]_{x}\) 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

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 compounds it fits. (b) Draw the structural formula for an aldehyde and a ketone with the molecular formula \(\mathrm{C}_{4} \mathrm{H}_{8} \mathrm{O}\). Give the systematic name of each.