Organic Chemistry Questions ___ 1. Molecules of 1-propanol and 2-propanol have different (1) percentage compositions; (2) molecular masses; (3) molecular formulas; (4) structural formulas. ___ 2. Which compound is an organic acid? (1) CH3CH2OH; (2) CH 3OCH3; (3) CH 3COOH; (4) CH3COOCH3. ___ 3. Each member of the alkane series differs from the preceding member by one additional carbon atom and (1) 1 hydrogen atom; (2) 2 hydrogen atoms; (3) 3 hydrogen atoms; (4) 4 hydrogen atoms. ___ 4. Which formula represents a saturated hydrocarbon? (1) C2H2; (2) C2H4; (3) C3H6; (4) C3H8. ___ 5. The members of the alkane series of hydrocarbons are similar in that each member has the same (1) empirical formula; (2) general formula; (3) structural formula; (4) molecular formula. ___ 6. What could be the name of a compound that has the general formula R-OH? (1) methanol; (2) methane; (3) methyl methanoate; (4) methanoic acid. ___

7.

A compound with the formula C6H6 is (4) pentene.

(1) toluene; (2) benzene; (3) butene;

___ 8.

C2H4 + H2 C2H6 The above reaction is an example of (2) substitution; (3) saponification; (4) esterification.

___

The compound C4H9OH is an isomer of (3) CH3COOC2H5; (4) CH 3COOH.

9.

(1)

(1) addition;

C3H7COCH3; (2) C 2H5OC2H5;

___ 10. What is the total number of carbon atoms contained in an ethyl group? (2) 2; (3) 3; (4) 4.

(1) 1;

___ 11. Which compound is a member of the alkane series? (1) C2H6; (2) C 3H6; (3) C 4H6; (4) C6H6. ___ 12. A reaction between an acid and alcohol produces an ester and (2) water; (3) glycerol; (4) ethanol. ___ 13. The general formula for the alkyne series is (4) CnH2n-2.

(1) carbon dioxide;

(1) CnHn ; (2) CnH2n; (3) Cn H2n+2;

___ 14. Which compound represents a member of the benzene series? (2) ethylene; (3) toluene; (4) propene. ___ 15. Which compound is an isomer of CH3COOH? (3) CH3CH2COOH; (4) CH 3COOCH3.

(1) HCOOCH3; (2) CH3CH2OH;

___ 16. Which compound is a member of the alkene series? (3) toluene; (4) ethene. ___

17.

(1) acetylene;

(1) benzene; (2) acetylene;

All carbon-carbon bonds in a saturated hydrocarbon molecule are

Organic Chemistry Questions

(1)

single

page 1 of 6

covalent; (2) double covalent; (3) triple covalent; (4) coordinate covalent. ___ 18. Which normal alkene has the highest boiling point at 1 atmosphere? (2) C3H6; (3) C4H8; (4) C5H10.

(1) C2H4;

___ 19. Which reaction produces ethyl alcohol as one of the principal products? (1) an esterification reaction; (2) a neutralization reaction; (3) a saponification reaction; (4) a fermentation reaction. ___ 20. Given the following reaction: C4H10 + Br 2 C4H9Br + HBr. The above reaction is an example of (1) substitution; (2) addition; (3) polymerization; (4) fermentation. ___ 21. In a molecule of C3H8, the total number of covalent bonds is (1) 11; (2) 10; (3) 3; (4) 8. ___ 22. Which compound is an ester? (4) CH3COCH3.

(1) CH3COOH; (2) CH 3CHO; (3) CH3COOCH3;

___ 23. The fermentation of C6H12O6 will produce carbon dioxide and (1) a polymer; (2) a soap; (3) an ester; (4) an alcohol. ___ 24. Compounds which have the same molecular formula but different molecular structures are called (1) isomers; (2) isotopes; (3) allotropes; (4) homologs. ___ 25. Which is the formula of a saturated hydrocarbon? (4) C5H12.

(1) C2H2; (2) C 2H4; (3) C 5H8;

___ 26. Cn H2n+2 is the general formula of a homologous series. Which is a member with this characteristic? (1) acetylene; (2) benzene; (3) propane; (4) toluene. ___ 27. A molecule of ethene is similar to a molecule of methane in that they both have the same (1) structural formula; (2) molecular formula; (3) number of carbon atoms; (4) number of hydrogen atoms. ___

28.

Which is the formula for ethanoic acid? (3) CH3CH2COOH; (4) CH 3CH2CH2OH.

___ 29. The compound CH3COOCH3 is classified as ester; (4) a hydrocarbon.

(1)

CH3COOH; (2) CH3CH2OH;

(1) an acid; (2) an alcohol; (3) an

___ 30. Each member in the alkane series of hydrocarbons, when considered in successive order, has 1 more carbon atom and how many more hydrogen atoms? (1) 1; (2) 2; (3) 3; (4) 4. ___ 31. Which molecular formula represents pentene? (4) C5H12.

(1) C4H8; (2) C4H10; (3) C5H10;

___ 32. A molecule of which alcohol contains more than one hydroxyl group? (1) propanol; (2) butanol; (3) pentanol; (4) glycerol. ___ 33. Hydrogen bonding is most noticable in (1) organic acids; (2) esters; (3) alkynes; (4) alkanes. Organic Chemistry Questions

page 2 of 6

___ 34. Which molecule contains a triple covalent bond? (4) C3H8.

(1) C2H2; (2) C2H4; (3) C3H6;

___ 35. Which formula represents an acid? (1) CH3COOCH3; (2) CH3OH; (3) CH3COOH; (4) CH3CH2CH3. ___ 36. Ethyl formate can be produced by heating concentrated sulfuric acid, ethyl alcohol and formic acid. This type of reaction is called (1) fermentation; (2) esterification; (3) saponification; (4) polymerization. ___ 37. Which formula represents a member of the alkene series? (3) C2H2; (4) C6H6.

(1) C3H6; (2) C2H6;

___ 38. Ethyne (acetylene) has which one of the following shapes? (1) tetrahedral; (2) planar triangular; (3) linear; (4) bent. ___ 39. Compared with organic compounds in general, organic compounds usually have (1) greater solubility in water; (2) a tendency to form ions more readily; (3) more rapid reaction rates; (4) lower melting points. ___ 40. Which represents the functional group of an organic acid? (3) -CHO; (4) -NH2. ___ 41.

(1) -COOH; (2) -OR;

C3H6 + H2 = C3H8 The above reaction is an example of (2) addition; (3) polymerization; (4) esterification.

(1) substitution;

___ 42. The isomers of propanol differ in (1) the number of carbon atoms; (2) molecular mass; (3) the arrangement of the carbon atoms; (4) the type of functional group. ___ 43. Which is the formula of an alcohol? (4) C5H11OH. ___ 44.

(1) Ba(OH)2; (2) HCHO; (3) CH3COOH;

C3H5(OH)3 The above organic compound is classified as (2) an ester; (3) an organic acid; (4) an alcohol.

(1) a carbohydrate;

___ 45. Which compound can have isomers? (1) C2H4; (2) C2H2; (3) C2H6; (4) C4H8. ___ 46.

C2H4 + Br2 = ? What reaction occurs when the above chemicals react? (1) polymerization; (2) substitution; (3) addition; (4) esterification.

___ 47. Which organic compound is a product of a fermentation reaction? (2) C2H2; (3) C2H5OH; (4) C2H5OC2H5.

(1) CCl2F2;

___ 48. Which organic compound is a product of an esterification reaction? (2) C3H7OH; (3) CH3COOH; (4) CH3COOCH3.

(1) C3H8;

___ 49. Which organic compound is a product of a saponification reaction? (2) C3H5(OH)3; (3) C6H6; (4) C6H12O6.

(1) CCl4;

___ 50. The structure of an alkene contains (1) only single bonds; (2) a double bond; (3) two double bonds; (4) a triple bond. ___ 51. As the members of the alkane series increase in molecular mass the magnitude of the van der Waals forces between the molecules (1) decreases; (2) increases; Organic Chemistry Questions

page 3 of 6

(3) remains the same. ___ 52. Which hydrocarbon has more than one possible structural formula? (2) C2H6; (3) C3H8; (4) C4H10.

(1) CH4;

___ 53. What is the number of hydrogen atoms in a molecule of ethyne? (1) 6; (2) 2; (3) 8; (4) 4. ___ 54. In an aqueous solution, which compound will be acidic? (1) CH3COOH; (2) C3H5(OH) 3; (3) CH3CH2OH; (4) CH 3OH. ___ 55. A process in which large molecules are broken down into smaller mole- cules is used commercially to increase the yield of gasoline from petroleum. This process is called (1) polymerization; (2) hydrogenation; (3) esterification; (4) cracking. ___ 56. Organic compounds must contain (1) oxygen; (2) nitrogen; (3) hydrogen; (4) carbon. ___ 57. The angle formed between any two carbon-hydrogen bonds in a molecule of an organic compound is a(an) (1) dihedral angle; (2) right angle; (3) tetrahedral angle; (4) acute angle. ___ 58. A specific arrangement of several atoms which gives characteristic properties to an organic molecule is known as a(an) (1) carboxyl group; (2) functional group; (3) group; (4) alkyl group. ___ 59. The ability of the carbon atom to form covalent bonds result in the formation of compounds that are (1) molecular; (2) ionic; (3) polar; (4) atomic. ___ 60. How many carbon atoms are in one molecule of 2,3,3-trimethyl- pentane? (2) 8; (3) 6; (4) 13.

(1) 5;

___ 61. The series of unsaturated hydrocarbons containing a triple bond shared between two adjacent carbon atoms is known as the (1) alkanes; (2) alkenes; (3) alkynes; (4) benzenes. ___ 62. Addition reactions occur in unsaturated hydrocarbons rather than in saturated hydrocarbons because unsaturated hydrocarbons (1) contain multiple bonds; (2) have a greater molecular mass; (3) have tetrahedral bonds; (4) contain more atoms. ___ 63. A dihydroxy alcohol that is made from ethane is (3) ethylene glycol; (4) ethane. ___ 64. A long chain protein is an example of a(an) (4) monomer.

(1) ethanol; (2) glycerol;

(1) fat; (2) polymer; (3) isomer;

___ 65. Which represents an unsaturated hydrocarbon? (4) C4H10.

(1) C2H4; (2) C2H6; (3) C 3H8;

___ 66. How many double bonds are in one molecule of 1,3-butadiene? (1) 1; (2) 2; (3) 3; (4) 4. ___ 67. Which is an isomer of 2-chloropropane? (1) butane; (2) propane; (3) 1-chlorobutane; (4) 1-chloropropane. Organic Chemistry Questions

page 4 of 6

___ 68. A fermentation reaction and a saponification reaction are similar in that they both can produce (1) an ester; (2) an alcohol; (3) an acid; (4) a soap. ___ 69. Which is a saturated hydrocarbon? (1) C3H8; (2) C6H6; (3) C2H5OH; (4) C2H4O 2. ___ 70. Which molecule will have a single pi bond? (1) benzene; (2) propene; (3) propane; (4) propyne. ___ 71. CH3CH2OH The above organic compound is classified as (2) an ester; (3) an alcohol; (4) an organic acid.

(1) a carbohydrate;

___ 72. Which organic molecule undergoes resonance? (1) benzene; (2) propyne; (3) methane; (4) ethanol. ___ 73. As the molecular mass of the compounds of the alkane series increases their boiling points (1) decreases; (2) increases; (3) remains the same. ___ 74. As the number of carbon atoms in the members of the alkene series increases, the ratio of carbon atoms to hydrogen atoms (1) decreases; (2) increases; (3) remains the same. ___ 75. Which compound is most likely to react by addition? (1) CH4; (2) C 3H6; (3) C4H10; (4) C5H12. ___ 76. Which alcohol contains three hydroxyl groups per molecule? (1) propanol; (2) glycerol; (3) butanol; (4) pentanol. ___ 77. Toluene belongs to the same series of hydrocarbons as (3) pentene; (4) butene. ___

78.

(1) benzene; (2) propene;

A hydrocarbon molecule containing one triple covalent bond is classified as an (1) alkene; (2) alkane; (3) alkyne; (4) alkadiene.

___ 79. Both cellulose and proteins are classified as (1) aldehydes; (2) esters; (3) polymers; (4) ketones. ___ 80. The compound 2-propanol is classified as a (1) primary alcohol; (2) secondary alcohol; (3) tertiary alcohol; (4) dihydroxy alcohol. ___ 81. What is the total number of hydrogen atoms in a molecule of butene? (1) 10; (2) 8; (3) 6; (4) 4. ___ 82. Which of the following compounds has the greatest possible number of isomers? (1) butane; (2) ethane; (3) pentane; (4) propane. ___ 83. Which is the correct molecular formula of pentene? (1) C5H8; (2) C 5H10; (3) C 5H12; (4) C5H14. ___ 84. The bonds between the atoms in an organic molecule are generally (2) coordinate covalent; (3) covalent; (4) hydrogen. ___

85.

(1) ionic;

As the length of the chain of carbon atoms in molecules of the alkene series increases, the number of double bonds per molecule (1) decreases; (2) increases;

Organic Chemistry Questions

page 5 of 6

(3) remains the same. ___

86.

In a condensation polymerization, the two products formed are a polymer and (1) water; (2) carbon dioxide; (3) an acid; (4) a base.

___ 87. Which is the correct molecular formula of 1,2-ethanediol? (1) C2H5OH; (2) C2H4(OH)2; (3) C3H5(OH)3; (4) C3H6(OH)2. ___ 88. In the reaction C2H5OH + CH3OH --> C2H5OCH3 + H2O, the organic compound formed is (1) an ester; (2) a ketone; (3) an acid; (4) an ether. ___ 89. Which compound is a saturated hydrocarbon? (1) ethene; (2) ethane; (3) ethylene; (4) ethyne. ___ 90. The compound C2H2 belongs to the series of hydrocarbons with the general formula (1) CnHn; (2) Cn H2n; (3) CnH2n-2 ; (4) CnH2n+2 . ___ 91. Which compound is a dihydroxyl alcohol? (1) Al(OH)3; (2) C3H5(OH) 3; (3) Ca(OH)2; (4) C2H4(OH)2. ___ 92. The name of the compound having the formula C3H5(OH)3 is (1) glycerol; (2) ethylene glycol; (3) propene; (4) propanoic acid. ___ 93. Which organic compound is a ketone? (1) CH3OH; (2) CH 3COCH3; (3) CH 3COOH; (4) CH3COOCH3. ___ 94. Which of the following compounds has the lowest normal boiling point? (1) butane; (2) ethane; (3) methane; (4) propane. ___ 95. Which process increases the yield of gasoline and kerosene from crude oil? (1) oxidation; (2) cracking; (3) Haber; (4) contact. ___ 96. Organic compounds that are essentially nonpolar and exhibit weak intermolecular forces have (1) low melting points; (2) low vapor pressure; (3) high conductivity in solution; (4) high boiling points. ___ 97. What is the formula for pentanol? (1) C5H12; (2) C5H11OH; (3) C 4H10; (4) C4H9OH. ___ 98. Which compound is a member of the alkene series of hydrocarbons? (2) propene; (3) toluene; (4) butadiene.

(1) benzene;

___ 99. Which compound contains a triple bond? (1) CH4; (2) C 2H2; (3) C 3H6; (4) C 4H10. ___ 100. Which organic reaction involves the bonding of monomers by a dehydration process? (1) substitution; (2) oxidation; (3) addition polymerization; (4) condensation polymerization. ___ 101. In crude petroleum, fractions can be separated according to their differing boiling points by (1) the contact process; (2) the Haber process; (3) fractional distillation; (4) cracking.

Organic Chemistry Questions

page 6 of 6

Name:____________________________

Unit VIII: Hydrocarbons test 3.1 Note: For clarity hydrogens have been omitted from most structures on this test. Whenever carbon does not appear to have the required number of bonds, it is understood that the “missing” bonds go to hydrogen atoms. Multiple Choice ___ 1. A saturated compound is one that (1) contains only carbon-carbon sigma bonds; (2) contains at least one carbon-carbon pi bond; (3) contains at least one carbon-carbon double or triple bond; (4) both 1 and 3; (5) both 2 and 3; (1,2) is not described by any of the above answers. ___ 2. Which of the following structures best describes an unsaturated compound? C

C

C

C

(1)

C C

C C (2)

(1,2) both 2 and 5

C C C C (3)

(1,3) all but 2

C

C C

C

C (4) (1,4) all but 5

C

C C C (5)

(1,5) all but 4 and 5

___ 3. The first three members of a homologous series are: CH4O, C2 H6O2 , C3 H8O 3. The fourth member of this series would be (1)C4 H10O4 ; (2) C4 H10O; (3) C 10H4O 4; (4) C 4H10O 2; (5) none of the above. ___ 4. The geometry associated with carbon-carbon triple bonds is (1) linear; (2) tetrahedral; (3) planar; (4) octahedral; (5) biplanar. ___ 5. Which of the following structures contain a chiral or asymmetric carbon atom? Cl Cl Cl I CH3 CH3 CH3 C Br I C CH3 C C C Br Br Br I (2) (1) (3)

Br C Br

Cl C

C Cl

(4)

___ 6. Isomers are compounds that (1) have the same number of carbon atoms but a different number of hydrogen atoms; (2) have the same number of hydrogen atoms but a different number of carbon atoms; (3) have the same number and kind of atoms in a molecule but differ in structure; (4) have the same kind of atoms in their molecular formulas but differ in the number of these atoms present; (5) none of the above. ___ 7. The two carbons joined by a triple bond in an alkyne are connected by (1) three sigma bonds; (2) one sigma bond and two pi bonds; (3) three pi bonds; (4) two identical sp3 bonds; (5) two sigma and one pi bond. Hydrocarbons test 3.1

1998

page 1 of 5

___ 8 Which of the following illustrate the process of hydrogenation? (1)

(2)

(3)

(4)

C

C

C

C

C

C

C

C

C

C

C

+

C

C

C

+

C

H2

C

C

C

C

H2

+

Br 2

C

C

C

C

C

C

C

C

C

+

C Br

C

C Br

H2 +

C

H2

___ 9. In a certain laboratory exercise Snoopy mixed 5 drops of a solution of bromine water with one milliliter of each of the following substances: butane, 2-butene, 1, butene, benzene, and methyl benzene. The experiment was carried out at room temperature. Which of the substances should react rapidly with the bromine? (1) butane; (2) 1-butene and 2-butene; (3) benzene and methyl benzene; (4) 2-butene and benzene; (5) all but butane. ___ 10. Whenever two or more equally valid structures can be drawn for a molecule involving only the relative positions of double and single bonds, ___________ is said to occur? (1) resonance; (2) geometric isomerism; (3) stereoisomerism; (4) cis configuration; (5) trans configuration. ___ 11. Which of the following best explain why there are so many carbon compounds? (1) concatenation; (2) isomerism; (3) multiple oxidation states are possible for carbon; (4) both 1 and 2; (5) both 2 and 3. ___ 12. Hydrogenation is the process of (1) adding hydrogen to unsaturated compounds; (2) adding hydrogen to saturated compounds; (3) removing hydrogen from saturated compounds; (4) removing hydrogen from unsaturated compounds. ___ 13. The formula for 2-nonacontene, an 90 carbon alkyne, would be (1)C90 H182 ; (2) C90 H180 ; (3) C90 H178 ; (4) C90 H176. ___ 14. In order to explain the geometry of organic compounds, among other properties, hybrid orbitals are postulated to exist. What type of hybridization exists for the carbon atom in order to explain the geometry associated with a carbon-carbon single bond? (1) sp3; (2) s3 p; (3) s2 p; (4) sp2 ; (5) sp. ___ 15. As explained in class, resonance structures occur when a (1) sigma bond attempts to form in two places at the same time; (2) pi bond attempts to form in two places at the same time; (3) two pi bonds attempt to form between adjacent hydrogen atoms; (4) two pi bonds attempt to form an arene without carbon atoms; (5) a hybrid warp orbital orientates perpendicular to the axis of a sigma-pi intercept vector involving six carbon atoms.

Hydrocarbons test 3.1

1998

page 2 of 5

Name: _____________________

Organic Compounds Test #3.1 Multiple Choice: Questions 1-14 pertain to the following structures. (Note: Where carbon does not have its required number of bonds, it is understood that the “missing” bonds go to hydrogen.)

(1) C C

(2) C

OH

C

C

(3) C

C

O

C

(4) C

C

C

C

C

O

OH C (5)

(1,4)

C

C

C

C

C

(1,2) C C SH

O

O C

C

(1,5) C

C

C

C NH 2

C

(1,3) C

(2,3)

C

C

C

C

C

C

C

C

OH

C

C

C C

C OH

C

NH 2

NH 2

(2,4)

C

(2,5) two or more of the above structures work

(3,4) none of the above structures are correct ___ 1. Which of the above is an example of a compound that would be produced by mild oxidation of a secondary alcohol? ___ 2. Is an organic acid? ___ 3. This structure is an example of a secondary alcohol? ___ 4. This structure is an example of an ester? ___ 5. This structure is an example of a thio or mercaptan? ___ 6. This structure is an example of a tertiary amine. ___ 7. The structure of ethyl propanoate. ___ 8. The structure of propyl ethanoate. Organic Compounds Test 3.1

1998

page 1 of 4

___ 9. The structure of 2 butanone. ___ 10. 2 propanone which is also known as acetone. ___ 11. The structure of a primary alcohol ___ 12. This structure could produce an amine if treated with H2, NH3, and heated. ___ 13. The structure of an aldehyde. ___ 14. Used to make diethyl ether. ___ 15. Which of the following is possible? (1) secondary ketone; (2) secondary aldehyde; (3) tertiary ketone; (4) secondary acid; (5) 1,2 and 3; (6) 2,3 and 4; (7) all of the above. ___ 16. In one of the laboratory investigations we took a look at the basic properties of alcohols. Based on our observations in that laboratory investigation, which of the following alcohols will react the fastest with HCl? (1) 1-pentanol; (2) 2-pentanol; (3) 1-butanol; (4) 2-butanol; (5) 2 methyl 3 pentanol; (1,2) 2 methyl, 2-pentanol. ___ 17. In the laboratory exercise on the properties and reactions of alcohols it was found that hot copper oxide would oxidize an alcohol. The alcohol we oxidized with hot copper oxide was methanol. What product would have been obtained if ethanol had been used in place of methanol? (1) ethanoate; (2) ethanal; (3) ethanoic acid; (4) ethanolamine; (5) none of the above. ___ 18. The rules for naming a ketone state that you are to name it as if it were derived from a hydrocarbon by dropping the final 'e' and adding (1) al; (2) ol; (3) one; (4) ous; (5) none of the above. ___ 19. Alkanes can be oxidized to alkenes with strong heating and a catalyst. This reaction is known as (1) hydrogenation; (2) dehydrogenation; (3) alkanation; (4) bromination; (5) none of the above. ___ 20. A test commonly used to detect an aldehyde is (1) Fehling’s test; (2) Benedict’s test; (3) Wagner’s test; (4) both 1 and 2; (5) both 2 and 3; (1,2) none of the above. ___ 21. Carbohydrates are monomers and polymers of aldehydes and ketones. They also contain the functional group of (1) alcohols; (2) esters; (3) amines; (4) acids. ___ 22. The difference between fats and oils from a chemist’s point of view is that (1) fats are usually unsaturated and oils are usually saturated; (2) oils are usually unsaturated and fats are usually saturated; (3) fats are polymers and oils are not; (4) oils are polymers and fats are not. ___ 23. Fats, oils, and waxes are (1) alochols; (2) acids; (3) aldehydes; (4) ketones; (5) ethers; (1,2) amines; (1,3) esters.

Organic Compounds Test 3.1

1998

page 2 of 4

___ 24. Which of the following structures illustrates an amino acid that might be important biologically, that is, be incorporated into proteins. H (1)

N

H

(3)

OH C H

H

H C O C C NH OH 2 H

N

H

H

H C

(2)

H

C C NH 3

O C

O

H (4)

OH

H2 N

C

OH

H

H C

OH

O C

OH

H

___ 25. Which of the following bonds would indicate a peptide bond?

(4)

H H H

N

C

O C

CH3

N H

(1)

H C

C

C H H

O

(2)

OH (3)

(5)

Short Answer Organic Compounds Test 3.1

1998

page 3 of 4

1. Show how to produce each of the following compounds. Each of these questions is worth three points--one point for the correct structure of the reactant, one point for the correct structure of the product, and one point for the proper conditions and/or inorganic reactants if any are required. The proper format is illustrated in the sample problem. (sample) show how to produce 2 methyl 2 chloro propane C

C C

C

HCl C

OH reactant (1 pt )

C

C

C Cl

conditions (1 pt)

product (1 pt)

a) propanoic acid

b) propyl ethyl ether

e) ethyl propanoate

Extra Credit What is the following?

I

O

N N

I

O

N

N

O

N N O

O

O

I

O N N O O

Organic Compounds Test 3.1

O

N

I

O N N N O

I

I

1998

page 4 of 4

___ 16. Which of the following illustrates the formation of a pi bond? (Note: The following legend applies to the various figures used in all answers.) Carbon atom

Carbon atom

•

p orbital s orbital

oribital overlap

(1)

+

oribital overlap

(2)

+

•

•

+

(3)

orbital overlap

oribital overlap

(4)

•

+

•

• •

___ 17. Which of the structures below is not an isomer of pentane?

C

C

C

C

C

C C

C

C C

C

C

C

C

C

C

C

C

C

C (1)

(2)

(3)

(4)

___ 18. The process of breaking up large hydrocarbon molecules into smaller molecules is known as (1) resonance; (2) hydrogenation; (3) dehydrogenation; (4) cracking.

Hydrocarbons test 3.1

1998

page 3 of 5

Matching Questions 19-29 pertain to the structures below and to the right. Match up the IUC name with a corresponding structure, if a structure exists.

C

C

C

C

C

C

C C

C

C

C

C

C C

C C

C

C

C

C

C

C

(4)

(3)

C

C

C

C C

(1)

C

C

C

C C

(1,2)

(5)

(2) CH3 C

___ 19. 2,3 dimethyl 1-butene

C

C

C

___ 20. 2,3 dimethyl 1-butyne

C

___ 21. 1, 3 dimethyl benzene

(1,3)

C

C

C

C

C

C

C

C C CH3

(1,4)

(1,5)

___ 22. 1, 4 dimethyl benzene CH3

___ 23. anthracene ___ 24. 3 methyl heptane

CH3

CH3 CH3

___ 25. 2 pentene

CH3

(2,3)

___ 26. hexane

(2,4)

CH3 (2,5)

___ 27. 3 ethyl pentane (3,5) no structure matches.

___ 28. an isomer of heptane (3,4) ___ 29. 2,3 dimethyl butane ___ 30. Which of the following is in favor of hurt?

C C (1)

Hydrocarbons test 3.1

C

C (2)

C

C

C

C

C C

C

C

C

C

(4)

(3)

1998

page 4 of 5

Short Answer 1. Name each of the six structures below. (Note: If you feel a structure cannot exist, for whatever reason, you must answer with “impossible”.)

a)

C2 H5

b) C

C2 H5

d)

C C

C C C

e)

C C

C

C C

C C C

c)

C C

C

C

f) C

C

C

C

C

C

C

C

C

C

C

a) _________________________

b) __________________________

c) _________________________

d) __________________________

e) _________________________

f) ___________________________

2. Draw a structure for benzene, showing all hydrogen atoms.

Hydrocarbons test 3.1

1998

page 5 of 5