Chapter 23

Give the molecular formula of an alkane with 25 carbon atoms.

Draw structural formulas of the five isomers of \(\mathrm{C}_{6} \mathrm{H}_{14}\).

Draw structural formulas of an alkane, a cycloalkane, an alkene, and an aromatic hydrocarbon, each with eight carbon atoms.

Explain why there are two isomers of 2 -butene. Draw their structural formulas and name the isomers.

Draw structural formulas for the isomers of ethylmethylbenzene.

Give condensed structural formulas of all possible substitution products of ethane and \(\mathrm{Cl}_{2}\).

Define the terms substitution reaction and addition reaction. Give examples of each.

What would you expect to be the major product when two molecules of HCl add successively to acetylene? Explain.

Write the structure of propylbenzene. Write the structure of \(p\) -dichlorobenzene.

What is a functional group? Give an example and explain how it fits this definition.

An aldehyde contains the carbonyl group. Ketones, carboxylic acids, and esters also contain the carbonyl group. What distinguishes these latter compounds from an aldehyde?

Identify and name the functional group in each of the following. A \(\mathrm{CH}_{3} \mathrm{COCH}_{3}\) B \(\mathrm{CH}_{3} \mathrm{OCH}_{2} \mathrm{CH}_{3}\) C \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CH}_{2}\) D \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOH}\) E \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CHO}\) F \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\)

The correct formula for butane is a \(\mathrm{C}_{2} \mathrm{H}_{6}\) b \(\mathrm{C}_{8} \mathrm{H}_{18}\) c \(\mathrm{CH}_{4}\) d \(\mathrm{C}_{4} \mathrm{H}_{10}\) e \(\mathrm{C}_{3} \mathrm{H}_{6}\)

Explain why you wouldn't expect to find a compound with the formula \(\mathrm{CH}_{5}\).

Catalytic cracking is an industrial process used to convert high-molecular- weight hydrocarbons to lowmolecular-weight hydrocarbons. A petroleum company has a huge supply of heating oil stored as straight-chain \(\mathrm{C}_{17} \mathrm{H}_{36},\) and demand has picked up for shorter chain hydrocarbons to be used in formulating gasoline. The company uses catalytic cracking to create the shorter chains necessary for gasoline. If they produce two molecules in the cracking, and 1-octene is one of them, what is the formula of the other molecule produced? As part of your answer, draw the condensed structural formula of the 1 -octene.

Why would you expect the melting points of the alkanes to increase in the series methane, ethane, propane, and so on?

Write an equation for a possible substitution reaction of ethane, \(\mathrm{C}_{2} \mathrm{H}_{6},\) with \(\mathrm{Br}_{2}\)

What is the major product when \(\mathrm{HBr}\) is added to methylpropene?

Write the condensed structural formula for each of the following compounds. a) 2,5 -dimethyloctane b) 4 -ethyl-2-methylheptane c) 3-ethylheptane d) 2,2,3,3 -tetramethylpentane

23.40 Write the condensed structural formula for each of the following compounds. a 2,2 -dimethylpentane b 2-ethyl-2-methylhexane c 3-ethyl-2-methyloctane d 3,4,4,5 -tetramethylheptane

Give the condensed structural formula for each of the following compounds. a 3-ethyl-2-pentene b 4 -ethyl-2-methyl-2-hexene

Write the condensed structural formula for each of the following compounds. a 2,3 -dimethyl-2-hexene b 2-methyl-4-propyl-3-decene

Give the IUPAC names and include the cis or trans label for each of the isomers of \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCH}_{2} \mathrm{CH}_{3}\).

Give the IUPAC names and include the cis or trans label for each of the isomers of \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCH}_{3}\).

Write structural formulas for a 1,1,1 -triphenylethane; b \(o\) -ethylmethylbenzene.

Write structural formulas for a 1,2,4 -trimethylbenzene b \(o\) -diethylbenzene.

Give the IUPAC name for each of the following. a. \(\mathrm{HOCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\)

Write the structural formula for each of the following compounds. a isopropyl propionate b \(t\) -butylamine c 2,2 -dimethylhexanoic acid d cis-3-hexene

Write the structural formula for each of the following compounds. a3-ethyl-1-hexene b 1,1,2 -triphenylethane c 1-phenyl-2-pentanone d cyclooctanone

Describe chemical tests that could distinguish between: a valeraldehyde (pentanal) and dipropylketone b \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{C}=\mathrm{C}-\mathrm{CH}=\mathrm{CH}_{2}\) and \(m\) -xvlene

Describe chemical tests that could distinguish between: a. acetic acid and acetaldehyde (ethanal) b. toluene (methylbenzene) and 2 -methylcyclohexene

Identify each of the following compounds. a. A gas with a sweetish odor that promotes the ripening of green fruit. b. An unsaturated compound of the formula \(\mathrm{C}_{7} \mathrm{H}_{8}\) that gives a negative test with bromine in carbon tetrachloride. c. A compound with an ammonia-like odor that acts as a base; its molecular formula is \(\mathrm{CH}_{5} \mathrm{~N}\). d. An alcohol used as a starting material for the manufacture of formaldehyde.

Identify each of the following compounds. a. An acidic compound that also has properties of an aldehyde; its molecular formula is \(\mathrm{CH}_{2} \mathrm{O}_{2}\). b. A compound used as a preservative for biological specimens and as a raw material for plastics. c. A saturated hydrocarbon boiling at \(0^{\circ} \mathrm{C}\) that is liquefied and sold in cylinders as a fuel. d. A saturated hydrocarbon that is the main constituent of natural gas.

A compound with a fragrant odor reacts with dilute acid to give two organic compounds, \(\mathrm{A}\) and \(\mathrm{B}\). Compound \(\mathrm{A}\) is identified as an alcohol with a molecular weight of 32.0 amu. Compound \(\mathrm{B}\) is identified as an aeid. It ean be reduced to give a compound whose composition is \(60.0 \% \mathrm{C}, 13.4 \% \mathrm{H},\) and \(26.6 \% \mathrm{O}\) and whose molecular weight is 60.1 amu. What is the name of the original compound?

For each of the following molecules, create the correct condensed structural formulas by adding and/ or removing hydrogen atoms (do not add or remove bonds). a \(\mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CH}\) b \(\mathrm{CH}_{3} \equiv \mathrm{CHCH}_{2} \mathrm{CH}_{2}\) c \(\mathrm{CH}_{3} \mathrm{CHC}=\mathrm{CCH}_{2}\)

Draw the condensed structural formulas for a primary, a secondary, and a tertiary alcohol, each containing five carbon atoms.

Write the condensed structural formulas of a ketone and an ester, each containing four carbon atoms.

You encounter a hydrocarbon with the name 2 -ethyl3-methylhexane. Is this a proper IUPAC name? If not, what is the proper IUPAC name? To answer this question, start by writing the condensed structural formula based on this name.

Write the condensed structural formula for each of the following. a An aldehyde that contains five carbon atoms. b An ether that contains four carbon atoms. c An aromatic hydrocarbon with methyl groups at positions 1 and 5 . d A secondary amine that contains five carbon atoms. An alkyne that contains four carbon atoms.

Draw the structural formula of the following hydrocarbons. a chlorobenzene b 4-methyl-2-hexene c \(n\) -octane d For each answer (a-c), indicate if the molecule is saturated or unsaturated.

For each of the following, write the condensed structural formula of a molecule that fits the description. Add hydrogen atoms to complete the structure. a An unsaturated alkene that contains five carbon atoms and one double bond. b An aromatic hydrocarbon that contains six carbon atoms and two fluorine atoms. c A saturated hydrocarbon that contains seven carbon atoms and one bromine atom at position number three on the carbon chain. d A secondary amine.

Amino acids are important biological molecules. Using the name amino acid as a guide, write the name and structure of the functional groups common to all amino acids.

Draw the cis and trans isomers of the compound 3 -methyl-3-hexene.

Complete and balance the reaction for each of the following undergoing a combustion reaction. a 2-methylpentane b 2,2-dimethylpropane c 3-methyl-3-hexene d 3-ethyl-3-propanol e ethylbenzene