CHM 2046C Chapter 12  Homework Packet    Name: _______________

Read Chapter 12

Chapter 12: Introduction to Organic Chemistry-Alkanes

A._____(02) Alkane Series Section 12.6 page 375 Table 12.2  Answers

B._____(04) Alkyl Radicals Section 12.6 page 376 Figure 12.3 Answers

B1.____(02) Additional Alkyl/Aryl Radicals (Research Internet)
C._____(04) Isomer Problem C6H14, C4H9Br, C3H6Br2 C5H10 Sections12.3,12.9,14.10

D._____(02) Recognition of 1o, 2o, 3o, 4o Carbons Section 12.6 page 376 (Lecture) Answers

E._____(02) Nomenclature Alkanes, Alkenes, Cycloalkanes Sections 12.6, 13.2,12.10Answers

E1_____(02) Nomenclature of Oxygen/Nitrogen Derivative

F._____(04) Functional Groups Section 12.2 Table 12.1 Page 361 Answers

_______(24) Chapter 12 Total


GOB McMurry 7th Table of Contents

12. Introduction to Organic Chemistry: Alkanes
12.1 The Nature of Organic Molecules
12.2 Families of Organic Molecules: Functional Groups
12.3 The Structure of Organic Molecules: Alkanes and Their Isomers
12.4 Drawing Organic Structures
12.5 The Shapes of Organic Molecules
12.6 Naming Alkanes
12.7 Properties of Alkanes
12.8 Reactions of Alkanes
12.9 Cycloalkanes
12.10 Drawing and Naming Cycloalkanes

GOB McMurry 7th Table of Contents
Alkenes, Alkynes, and Aromatic Compounds
13.1 Alkenes and Alkynes
13.2 Naming Alkenes and Alkynes
13.3 The Structure of Alkenes: Cis—Trans Isomerism
13.4 Properties of Alkenes and Alkynes
13.5 Types of Organic Reactions
13.6 Reactions of Alkenes and Alkynes
13.7 Alkene Polymers
13.8 Aromatic Compounds and the Structure of Benzene
13.9 Naming Aromatic Compounds
13.10 Reactions of Aromatic Compounds


Module 16 Alkane Series   2 points

Name the first ten members of the alkane series and give its chemical, semi-structural, or structural  formula:

                             Name                                          Chemical Formula






























Reading Reference: GOB McMurry 7th Section 12.6 Table 12.2 Page 375

Chapter 12  Part B: Alkyl Radicals   4 points


Draw the structural or semi-structural formulas for all the alkyl radicals of the first four members of the alkane series, insert a X in place of the hydrogen which is removed to make the radical:


Methyl                                                                                                Ethyl










n-propyl                                                                                          isopropyl











n-butyl                                                                                               sec-butyl










Isobutyl                                                                                 t-butyl or tert-butyl














Reading Reference: GOB McMurry 7th Section 12.6 Page 376



Chapter 12 Part B1: Additional Alkyl and Aryl Radicals   2 points

Draw the structural or semi-structural formulas for all the alkyl/aryl radicals of the following. Place a X in place of the hydrogen which is removed to make the radical: (Not in Chapter 12-use the Internet)

n-pentyl (amyl)                             isopentyl or isoamyl








neopentyl                                    sec-amyl or sec-pentyl









Allyl                                             vinyl












Additional Alkyl and Aryl Radicals


Benzyl                                        phenyl








o-tolyl                               m-tolyl                                 p-tolyl








Naming Organic Compounds:

IUPAC Rules for Alkane Nomenclature

 1.   Find and name the longest continuous carbon chain.
 2.   Identify and name groups attached to this chain.
 3.   Number the chain consecutively, starting at the end nearest a substituent group.
 4.   Designate the location of each substituent group by an appropriate number and name.
 5.   Assemble the name, listing groups in alphabetical order using the full name (e.g. cyclopropyl before isobutyl).
    The prefixes di, tri, tetra etc., used to designate several groups of the same kind, are not considered when alphabetizing.

Web Page: Structure and Nomenclature of Hydrocarbons:


Chapter 12 Part C: Structural Isomer Number Problem:

Alkanes, Alkyl halides, and Cycloalkanes   4 points (Similar Test  Item)


Draw the structural or semi-structural formulas for all the isomers of the following chemical formulas, then give the IUPAC name for each:

(do all eight for homework)


#1   C5H12  and C4H10   5 total isomers;    or      C6H14   5 isomers;  Answers    


#2   C4H9Br  4 isomers; Answers           or         C3H6Br2   4 isomers; Answers


#3   C5H10  5 isomers (cycloalkanes only);  or  C5H10  5 isomers (alkenes only)    


#4   C6H4Br2  3 aromatic isomers       or          C7H7Br2  6 aromatic dibromo toluenes



Test Item #1

C6H14  5 aliphatic alkane isomers
















C5H12 and C4H10   5 total isomers between the two aliphatic alkanes



















Test Item #2

C4H9Br     4 isomers (alkyl halides)
















C3H6Br2  4 isomers (alkyl dihalides)


















      Cycloalkanes have one or more rings of carbon atoms. The simplest examples of this class consist of a single, unsubstituted carbon ring, and these form a homologous series similar to the unbranched alkanes. The IUPAC names of the first five members of this series are given in the following table. The last (yellow shaded) column gives the general formula for a cycloalkane of any size. If a simple unbranched alkane is converted to a cycloalkane two hydrogen atoms, one from each end of the chain, must be lost. Hence the general formula for a cycloalkane composed of n carbons is CnH2n. Although a cycloalkane has two fewer hydrogens than the equivalent alkane, each carbon is bonded to four other atoms so such compounds are still considered to be saturated with hydrogen.

Examples of Simple Cycloalkanes


















Substituted cycloalkanes are named in a fashion very similar to that used for naming branched alkanes. The chief difference in the rules and procedures occurs in the numbering system. Since all the carbons of a ring are equivalent (a ring has no ends like a chain does), the numbering starts at a substituted ring atom.

IUPAC Rules for Cycloalkane Nomenclature

 1.   For a monosubstituted cycloalkane the ring supplies the root name (table above) and the substituent group is named as usual. A location number is unnecessary.
 2.   If the alkyl substituent is large and/or complex, the ring may be named as a substituent group on an alkane.
 3.   If two different substituents are present on the ring, they are listed in alphabetical order, and the first cited substituent is assigned to carbon #1. The numbering of ring carbons then continues in a direction (clockwise or counter-clockwise) that affords the second substituent the lower possible location number.
 4.   If several substituents are present on the ring, they are listed in alphabetical order. Location numbers are assigned to the substituents so that one of them is at carbon #1 and the other locations have the lowest possible numbers, counting in either a clockwise or counter-clockwise direction.
 5.   The name is assembled, listing groups in alphabetical order and giving each group (if there are two or more) a location number. The prefixes di, tri, tetra etc., used to designate several groups of the same kind, are not considered when alphabetizing.


Test Item #3

C4H8  5 total isomers (cycloalkanes plus alkenes)   

















C5H10  5 total isomers (cycloalkanes only)

















IUPAC Rules for Alkene and Cycloalkene Nomenclature

 1.   The ene suffix (ending) indicates an alkene or cycloalkene.
 2.   The longest chain chosen for the root name must include both carbon atoms of the double bond.
 3.   The root chain must be numbered from the end nearest a double bond carbon atom. If the double bond is in the center of the chain, the nearest substituent rule is used to determine the end where numbering starts.
 4.   The smaller of the two numbers designating the carbon atoms of the double bond is used as the double bond locator. If more than one double bond is present the compound is named as a diene, triene or equivalent prefix indicating the number of double bonds, and each double bond is assigned a locator number.
 5.   In cycloalkenes the double bond carbons are assigned ring locations #1 and #2. Which of the two is #1 may be determined by the nearest substituent rule.
 6.   Substituent groups containing double bonds are:
2C=CH–   Vinyl group
2C=CH–CH2   Allyl group


C5H10  5 total isomers (alkenes only)
































Chapter 12  Part D: Recognition of 1o, 2o, 3o, 4o carbons & 1o, 2o, 3o hydrogen 2 points

Classify the carbon or hydrogen atom in the below structure as 1o, 2o, 3o, 4o

or primary, secondary, tertiary, or neo (or quaternary)  carbon or hydrogen atoms: The numbers below on each image refer to the parent hydrocarbon of the chain::

Image #2





1. C1:_____

2. C2: _____

3. H2: _____

4. C4: _____

5. C5 :_____

6. C6: _____



7. C5: _____

8.  C3:_____

9.  C2:_____

10. C1:_____



11. C5:_____

12. C4:_____

13. H3_____

14. C2:_____

15.C1: _____



16. C5:_____

17. H4:_____

18. C3:_____

19. C2:_____

20. C1:_____






Module 16   Part E: Nomenclature of Alkanes and Cycloalkanes   2 points


Give the IUPAC Name for the following compounds:





1. ___________________________






2. ___________________________








3. ____________________________







4. ___________________________






5. ___________________________










Classification of Organic Compounds Via Functional Groups








Chapter 12 Part F: Functional Group Recognition   2 points

 Classify the following compounds according to their Functional Group: See Table 12.1 Page 361

A. Alkane                     F. Aromatic Hydrocarbon   K. Ketone               P. Amide

B. Alkene                     G. Alkyl/Aryl Halide             L. Carboxylic Acid

C. Alkyne                     H. Alcohol                           M. Ester          

D. Cycloalkane               I.  Ether                              N. Amine

E. Cycloalkene              J.  Aldehyde                       O. Amino Acid

1. ___

2. ___

3. ___

4. ___

5. ___

6. ___

7. ___

8. ___

9. ___

10. __

11. __

12. __

13. __

14. __

15. __

16. __

1.   2.    3.     4.

5.        6.    7.  

8. 9.

10.     11.12.    13.14.   15. 16.

Chapter 12 Part E1: Nomenclature Organic Oxygen/Nitrogen Derivatives 2 points

  1.      ________________________


  1.    _________________________


  1.             _________________________


  1.    ___________________________


  1.    ______________________________


  1.                         _______________________________


  1.          ________________________________

Reading Reference: GOB McMurry 7th Sections 12.3, 16.2, 17.1 and 15.1: