Question: An ester is similar to a carboxylic

> 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

> Draw the structure of the monomer and the basic repeating unit for each of the following polymeric substances. a. polyethylene b. polyvinyl chloride c. Teflon d. polypropylene e. polystyrene

> Draw a structural formula for each of the following. a. 3-methylbutanoic acid b. 2-chlorobenzoic acid c. hexanoic acid d. acetic acid

> Draw the structural formula for each of the following straightchain alkanes. a. pentane b. undecane (11 carbon atoms) c. nonane d. heptane

> How are carboxylic acids synthesized? Give an example of an organic acid and the molecule from which it is synthesized. What type of reaction is this?

> Assign oxidation states to all of the atoms in each of the following. a. CuCl2 b. KClO3 c. KClO4 d. Na2CO3

> Draw a structural formula for each of the following alcohols. Indicate whether the alcohol is primary, secondary, or tertiary. a. 2-propanol b. 2-methyl-2-propanol c. 4-isopropyl-2-heptanol d. 2,3-dichloro-1-pentanol

> On the basis of the functional groups listed in Table 20.5, identify the family of organic compounds to which each of the following belongs. a. CH2-CH,-C=0 OH b. CH,—CH, — Сн, —ҫ-о CH,-CH,-C=0 0-CH2-CH,- d. OH -CH2-CH,

> Name each of the following aromatic or substituted aromatic compounds. a. с. -CH; - NO, -CH3 b. Br Br d. Br

> Draw structural formulas showing all the isomers of the straight-chain alkyne with eight carbon atoms. Name each isomer.

> Write the formula for the missing reactant or product in each of the following chemical equations. a. CH4(g) + Cl2(g) + HCl(g) b. CH3CH2CH3(g) CH3CH=CH2(g) + c. CHCl3(l) + Cl2(g) CCl4(l) +

> Draw a structural formula for each of the following compounds. a. 2,2-dimethylhexane b. 2,3-dimethylhexane c. 3,3-dimethylhexane d. 3,4-dimethylhexane e. 2,4-dimethylhexane

> Give the systematic name for each of the following alkanes. CH, a. CH,-CH-CH–CH, ČH, b. CH,-CH, CH,-CH, CH,-CH, `CH,-CH, с. СH, CH, CH-C-CH,-CH,-CH, CH, ČH, d. CH,-CH-CH-CH-CH-CH-CH, CH, CH, CH, сн, сH,

> Give the name of each of the following straight-chain alkanes. a. CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH3 b. CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH3 c. CH3-CH2-CH2-CH2-CH2-CH3 d. CH=-CH2-CH2-CH3

> Draw structural formulas for all isomeric alkanes having the general formula C7H16.

> Draw a structural formula for each of the following aromatic compounds. a. 1,2-dichlorobenzene b. 1,3-dimethylbenzene c. 3-nitrophenol d. p-dibromobenzene e. 4-nitrotoluene

> Consider the three isotopes of magnesium discussed in Exercise 17. Given that the relative natural abundances of these isotopes are 79%, 10%, and 11%, respectively, without looking at the inside cover of this book, what is the approximate atomic molar ma

> Complete the following table with the name or structure as needed.

> Alpha amino acids are organic acid molecules that also happen to contain an amino group (-NH2) on the second carbon atom of the acid’s chain. Proteins are condensation polymers of such alpha amino acids. The reaction by which the long c

> Salicylic acid is an interesting molecule; it is both an acid and an alcohol, having a hydroxyl group attached to the aromatic ring (phenol). For this reason, salicylic acid can undergo two different esterification reactions depending on which functional

> Write a structural formula for each of the following compounds. a. methyl pentyl ketone b. 3-methylpentanal c. 2-methyl-1-pentanol d. 1,2,3-propanetriol e. 2-methyl-3-hexanone

> Draw a structure corresponding to each of the following names. a. 2-methylpentanal b. 3-hydroxybutanoic acid c. 2-aminopropanal d. 2,4-hexanedione e. 3-methylbenzaldehyde

> On the basis of the functional groups listed in Table 20.5, which of the following organic functional groups does not contain any oxygen atoms? a. halohydrocarbons b. ethers c. esters d. aldehydes e. amines From Table 20.5: Class Functional Gro

> The alcohol glycerol (glycerine), which is produced in the human body by the digestion of fats, has the following structure. Give the systematic name of glycerol. CH,-CH-CH, -CH- OH он ОН

> How many of the following alcohols are secondary alcohols? a. ethanol b. isopropyl alcohol c. tert-butyl alcohol d. methanol

> Without drawing a structural formula, tell how many hydrogen atoms would be present in the straight-chain alkanes with the following numbers of carbon atoms. a. 4 b. 6 c. 17 d. 20

> Draw the structural formula(s) for, and give the name(s) of, the organic product(s) of each of the following reactions. If a mixture of several, similar products is expected, indicate the type of product expected. Light a. CH;-CH; + Cl, Pt b. CH,-CH=

> What is the oxidation state of chlorine in each of the following substances? a. ClF b. Cl2 c. HCl d. HClO

> Write a structural formula for each of the following compounds. a. 2,3-dimethylheptane b. 2,2-dimethyl-3-chloro-1-octanol c. 2-chloro-1-hexene d. 1-chloro-2-hexene e. 2-methylphenol

> Give some examples of molecules containing “fused” benzene rings.

> Give the systematic name for each of the following unsaturated hydrocarbons and substituted unsaturated compounds. а. CH,— CH3CH-CH, b. CH;-CH-CH=CH, ČH, c. CH=C-CH,–CH, d. CH,=CH-CH–CH, CI

> How many of the following organic functional groups must contain two oxygen atoms? a. alcohols b. esters c. carboxylic acids d. ketones e. aldehydes

> What does it mean to say that a hydrocarbon is saturated? To how many other atoms is each carbon atom in a saturated hydrocarbon bonded? What name is given to the family of saturated hydrocarbons?

> Show (by drawing structures) how the members of a series of alkanes differ from the previous or following member of the series by a -CH2- unit.

> For each of the following straight-chain alkanes, draw the structural formula. a. ethane b. butane c. hexane

> The typically sweet-smelling compounds called result from the condensation reaction of an organic acid with a(n) .

> Which of the following is not an organic molecule? a. methanol b. acetone c. acetic acid d. magnesium sulfate e. All of the above are organic molecules.

> What is the “general” formula for an alkane? Show how this general formula can be used to determine the number of hydrogens that would be present for an alkane with 20 carbon atoms.

> What is a positron? What are the mass number and charge of a positron? How do the mass number and atomic number of a nucleus change when the nucleus produces a positron?

> Aldehydes and ketones can be prepared by of the corresponding alcohol.

> Both aldehydes and ketones contain the group, but they differ in where this group occurs along the hydrocarbon chain.

> Ethanol is commonly prepared by the of certain sugars by yeast.

> The simplest alcohol, methanol, is prepared industrially by the hydrogenation of .

> A(n) alcohol is one in which there is only one hydrocarbon group attached to the carbon atom holding the hydroxyl group.

> An atom or group of atoms that imparts new and characteristic properties to an organic molecule is called a(n) group.

> Benzene is the parent member of the group of hydrocarbons called hydrocarbons.

> Unsaturated fats may be converted to saturated fats by the process of .

> Alkenes and alkynes are characterized by their ability to undergo rapid, complete reactions, by which other atoms attach themselves to the carbon atoms of the double or triple bond.

> With very reactive agents, such as the halogen elements, alkanes undergo reactions, whereby a new atom replaces one or more hydrogen atoms of the alkane.

> What is the oxidation state of sulfur in each of the following substances? a. S8 c. NaHSO4 b. H2SO4 d. Na2S

> The chains in normal alkanes are not really straight but zigzag because the bond angles around the carbon atoms are .

> What makes carbon able to form so many different compounds?

> Rank these organic compounds in terms of increasing water solubility (from least water soluble to most water soluble). CH;CH;CH2COH CH3 b. CH;CH2CH=¢ ČH3 CH;CH2CH¿CH3 c.

> Esterification reactions are carried out in the presence of a strong acid such as H2SO4. A carboxylic acid is warmed with an alcohol, and an ester and water are formed. You may have made a fruity-smelling ester in the lab when studying organic functional

> Name each of the following organic compounds.

> Name each of the following alkenes and alkynes. CH3 a. CH3CH2-C==CH2 CH3 CH3 b. CH2=ċ-CH2-ċ=CH2 CH3 c. CH3CH2CH-CH=CH-CH2CH CH2CH3 CH3 d. CH;CH,CH,CH;CH-C=CH Br CH3 CH3 e. CH3-Ċ-C=C-CH ČH;CH2 CH3 CI CH,CH3 f. HC=C-CH-CH CH3 CH2CH2CH2CH3