Question: Without looking back at the text, write

> The sum of the numbers of neutrons and protons is the .

> What does the atomic number of an atom represent?

> How large is a typical atomic nucleus, and how does the size of the nucleus of an atom compare with the overall size of the atom?

> The major use of alkanes has been in reactions, as a source of heat and light.

> Tetraethyl lead, (C2H5)4Pb, was added to gasoline in the past as a(n) agent.

> Kerosene may be converted to gasoline by , which means that the larger, heavier kerosene components are broken down by heat into smaller, lighter gasoline fragments.

> The “Chemistry in Focus” segment Do We Age by Oxidation? discusses antioxidants. What does it mean for a chemical to be an antioxidant? How would it work chemically?

> 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.

> For a branched hydrocarbon, the root name for the hydrocarbon comes from the number of carbon atoms in the continuous chain in the molecule.

> 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.

> Structural isomerism occurs when two molecules have the same number of each type of atom but exhibit different arrangements of the between those atoms.

> Alkanes in which the carbon atoms form a single unbranched chain are said to be alkanes.

> The general orientation of the four pairs of electrons around the carbon atoms in alkanes is .

> A carbon compound containing a carbon–carbon double or triple bond is said to be .

> Figure 20.3 shows the structures of the hydrocarbons propane and butane. Discuss the arrangement of the electron pairs around each of the carbon atoms in these molecules. Are these molecules linear? Why or why not? From figure 20.3: 109.5° H H H H.

> The first “organic” compound to be synthesized in the laboratory, rather than being isolated from nature, was , which was prepared from .

> For the polymeric substances nylon and Dacron, sketch representations of the repeating unit in each.

> Does an oxidizing agent donate or accept electrons? Does a reducing agent donate or accept electrons?

> What are some applications of the common polymer polyvinyl chloride (PVC)?

> The “Chemistry in Focus” segment Mother of Invention discusses Stephanie Kwolek and the invention of Kevlar. Is Kevlar a copolymer or a homopolymer?

> What is condensation polymerization, and how does it differ from addition polymerization? Give an example of a common condensation polymer.

> One type of polymerization reaction in which the monomers “add together” to form the polymer (and no other products are formed) is called a(n) polymerization.

> What, in general terms, is a polymer? What is a monomer?

> Draw a structural formula for each of the following: a. methyl butanoate b. ethyl acetate c. o-chlorobenzoic acid d. 2,2-dimethyl-3-chloro-butanoic acid

> Give the systematic name for each of the following organic acids: a. CH,-CH,-CH-C CH, HO CH,-C b. CH, c. CH,-CH,-ċ–CH,-C HO. CH3 CH, c-CH,-Ċ-CH, d. Но ČH, CI

> What two main functional groups are in acetylsalicylic acid (aspirin)?

> Which of the following molecules are saturated? a. CH3-CH3 b. CH2=CH2 c. CH3-CH2-CH2-CH3 d. CH3-CH2-CH=CH2

> From what two families of organic compounds are esters synthesized? Give a specific example of a reaction in which an ester is formed, and indicate how the name of the ester in your example is derived from the compounds used to synthesize it.

> Does an oxidizing agent increase or decrease its own oxidation state when it acts on another atom? Does a reducing agent increase or decrease its own oxidation state when it acts on another substance?

> Complete the following equations with the structural formula of the principal organic product. / Mild oxidation а. CH, — CH, —CH,—CH,—Он Strong oxidation b. CH, — CH, —CH,—ОН

> Are carboxylic acids typically strong acids or weak acids? Write an equation showing the acid CH3CH2COOH ionizing in water.

> Draw the structure of the group that characterizes organic (carboxylic) acids. Give the general condensed formula for an organic acid.

> Draw structural formulas for each of the following aldehydes and ketones. a. dimethyl ketone b. 3-methyl-2-butanone c. propanal d. 2,2-dimethyl-3-pentanone

> Give the systematic name for each of the following aldehydes or ketones. CH3 a. CH,-CH- CH,-C-C H CH3 CH, b. CH,-CH- c-CH-CH, CH, Ö CH, CH, CI c. CH,-C-ČH-CH, d. CH,-C H.

> Provide an alternative name for the compound 2-butanone.

> Aldehydes and ketones both contain the carbonyl group, yet the properties of these two types of compounds are different enough that they are classified separately. Without looking back at the text, draw the structures of the ketone and the aldehyde that

> Write equations showing the oxidation of a primary alcohol and the oxidation of a secondary alcohol to produce an aldehyde and a ketone, respectively. Indicate the structure of each alcohol and of the principal organic products of the oxidations.

> Which of the following molecules are unsaturated? a. CH3-CH2-CH2-CH3 b. CH3-CH=CH-CH3 c. CH3-C (C-CH3 d. CH3-CH2-CH3

> What is acetone commonly used for in industry? What compound gives rancid butter its unpleasant odor?

> What is an oxidizing agent? What is a reducing agent?

> What functional group is common to both aldehydes and ketones?

> What is the simplest aromatic alcohol commonly called? What is it mostly used for in the United States?

> Write the equation for the fermentation of glucose to form ethanol. Why can’t ethanol solutions of greater than about 13% concentration be made directly by fermentation? How can the ethanol content be increased beyond this level in beverages?

> Is 1-pentanol a primary, secondary, or tertiary alcohol? Why or why not?

> Give the systematic name for each of the following alcohols. Indicate whether the alcohol is primary, secondary, or tertiary. CH,-CH3 а. CH —CH, —с-сн,—сH, ÓH CH3 CH3 b. CH;-CH-CH-CH-CH3 CH3 c. CH3-CH-CH,-C-CH3 CH3 d. CH;-CH-CH,-C-CH,-OH CH3 CH3

> Distinguish among primary, secondary, and tertiary alcohols. Give a structural formula for an example of each type.

> Draw the Lewis structures for carbon dioxide and carbon monoxide.

> What functional group characterizes an alcohol? What ending is added to the name of the parent hydrocarbon to show that a molecule is an alcohol?

> Based on the functional group each molecule below contains, identify the family of organic compounds to which each belongs. CH;-CH,-C a. OH b. CH3-CH2-CH,-C `H. c. CH,-CH,-CH,-Ċ-CH,-CH3 CH,-CH; d. CH3-CH,-C-CH,-CH; ОН

> Reduction can be defined as a gain of electrons or as a decrease in oxidation state. Explain why the two definitions mean the same thing, and give an example to support your explanation.

> Name the following aromatic or substituted aromatic compounds. а. CH3- Br Br b. CH3 с. ÓH d. NO2 NO,

> Draw a structural formula for each of the following aromatic or substituted aromatic compounds. a. naphthalene b. 2-bromophenol c. 3-methylstyrene d. 4-nitrochlorobenzene e. 1,3-dinitrobenzene

> What do the prefixes ortho-, meta-, and para- refer to in terms of the relative location of substituents in a disubstituted benzene?

> How is the benzene ring named if it is considered a substituent in another molecule? Give the structures and names of two examples.

> How is a monosubstituted benzene named? Give the structures and names of two examples. Also give two examples of monosubstituted benzenes that have special names.

> When a carbon atom is bonded to four other atoms, what geometric arrangement occurs around the carbon atom? Why?

> What structure do all aromatic hydrocarbons have in common?

> Draw structural formulas showing all possible molecules containing six carbon atoms and having one triple bond.

> Draw structural formulas and give the systematic names for at least four isomeric hydrocarbons containing seven carbon atoms and one double bond.

> Give the systematic name for each of the following unsaturated hydrocarbons. CI а. СН,—СH— СH-CH—СH ČH, CH, ĊI CH, b. СH, —СH3CH-CH—СH ČI ČI CH3 с. СH, — С—СH—CH—СH— CH— CH, CH, CH3 d. CH=C-CH,-CH,-CH-CH3 ČH,

> Oxidation can be defined as a loss of electrons or as an increase in oxidation state. Explain why the two definitions mean the same thing, and give an example to support your explanation.

> Give the systematic name for each of the following unsaturated hydrocarbons. а. СH; — CH—CH-CH, — СH; b. CH;-CH,-CH=CH-CH; с. СH;—СH- CH-CH—СH-CH; CH3 d. CH,3CH- СH-CH—CH -CH,—СH; CH3 CH3 CHz

> How is hydrogenation used in the production of solid shortenings for cooking? Give an example of a hydrogenation reaction.

> Indicate the missing molecule in each of the following reactions of alkenes. a. CH2=CH–CH3 + H2 / ? b. ? + Br2 / CH2Br–CHBr–CH3 c. 2CH2=CH–CH3 + 9? / 6CO2 + 6H2O

> How is the location of a double or triple bond in the longest continuous chain of an unsaturated hydrocarbon indicated?

> How is the root name of an alkane modified to indicate that a given hydrocarbon contains a double or triple bond in its longest continuous chain?

> What is an alkyne? What structural feature characterizes alkynes? Give the general formula for alkynes.

> How many electron pairs are shared when a triple bond exists between two carbon atoms? What must be the geometric arrangement around the carbon atoms in a triple bond? Draw the Lewis structure of a simple molecule that contains a triple bond.

> What is an alkene? What structural feature characterizes alkenes? Give the general formula for alkenes.

> Complete and balance each of the following chemical equations. a. C8H18(l) + O2(g) ( b. CH3Cl(l) + Cl2(g) ( c. CHCl3(l) + Cl2(g) (

> Complete and balance each of the following combustion reactions of alkanes. a. C2H6(g) + O2(g) / b. C4H10(g) + O2 / c. C3H8(g) + O2(g) /

> Assign oxidation states to all of the atoms in each of the following ions. a. NH4+ c. OH- b. HCO3- d. Cr2O72-

> When an alkane molecule undergoes a(n) reaction, hydrogen atoms are removed, and the product is an unsaturated hydrocarbon.

> Indicate the missing molecule in each of the following substitution reactions. a. CH4 + Cl2 hv HCl + ? b. CH2Cl2 + Cl2 hv CHCl3 + ? c. ? + Cl2 hv CCl4 + HCl d. CH3Cl + ? hv CH2Cl2 + HCl

> Write an equation showing the combustion of propane, C3H8. How do we make use of combustion reactions?

> Explain why alkanes are relatively unreactive.

> Why was tetraethyl lead, (C2H5)4Pb, added to gasoline in the past? Why is the use of this substance being phased out?

> What is pyrolytic cracking, and why is the process applied to the kerosene fraction of petroleum?

> To be used efficiently, petroleum must be separated by boiling into portions called .

> What does a double bond represent? How many pairs of electrons are shared between the atoms in a double bond? Draw the Lewis structure of a simple molecule that contains a double bond.

> What are the major constituents of crude petroleum? What is the major constituent of natural gas? How were these mixtures formed?

> Draw a structural formula for each of the following branched alkanes. a. 2,2,4-trimethyloctane b. 2,3,4-trimethyloctane c. 3,3,4-trimethyloctane d. 2,4,4-trimethyloctane

> Assign oxidation states to all of the atoms in each of the following ions: a. CO32- b. NO3- c. PO43- d. SO42-

> Draw a structural formula for each of the following branched alkanes. a. 2,3-dimethylpentane b. 2,4-dimethylpentane c. 2,2-dimethylpentane d. 3,3-dimethylpentane

> Give the systematic name for each of the following alkanes. а. CH, —CH,—СH -СH,—CH, ČH,-CH, CH, b. CH;-C-CH3 CH,-CH3 c. CH, CH, CH3 CH, d. CH,-CH-CH–CH-CH, CH, CH3 CH,

> Give the systematic name for each of the following branched alkanes. a. CH;-CH,-CH,–CH-CH-CH,–CH,-CH, ČH; CH, ČH3 CH, CH, b. CH,-CH, —Сн,-с—с-сн,—CH, CH, CH, CH, с. СН,—СH,—CH-CH—С-СH,—CH, CH, CH3 CH3 CH; CH, d. CH;-CH,-CH–CH–CH-CH; 1. CH, ČH;

> When naming alkanes, the alkyl groups are listed in alphabetical order, disregarding any .

> What prefixes would be used in the systematic name of an alkane to indicate that the alkane contained the following numbers of methyl branches? a. two b. four c. five d. three

> When naming alkanes, find the longest continuous chain of carbon atoms. This chain (called the chain) determines the base alkane name.

> What is an alkyl group? How is a given alkyl group related to its parent alkane?

> To what does the root name for a branched hydrocarbon correspond?

> Your roommate, a chemistry major, claims to have synthesized the compound CH5 in the lab. Why is that not possible?

> Give the root names for the alkanes with three, five, seven, and nine carbon atoms.

> Assign oxidation states to all of the atoms in each of the following. a. MgO b. Fe2O3 c. PCl3 d. N2O5

> How do chemists define the processes of oxidation and reduction? Write a simple equation illustrating each of your definitions.

> Draw structural formulas for three isomeric alkanes having the formula C6H14.

> Without looking back at the text, draw structural formulas and give the common names for the three isomers of pentane, C5H12.

> What is a branched alkane? Draw the structure of a branched alkane and circle the branch.

> What are structural isomers? Which is the smallest alkane that has a structural isomer? Draw structures to illustrate the isomers.

> Name each of the following alkanes. a. CH3-CH2-CH2–CH2-CH3 CH3 CH3 b. CH3-CH-ÇH–CH2-CH CH2 CH3 ČH3 CH3 CH-CH3 c. CH3-CH2-CH2-CH-CH-CH,-CH2-CH3 CH3-CH2