Chapter 12 Homework Packet

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 Answers

D._____(02) Recognition of 1^o, 2^o, 3^o, 4^o 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 7^th 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 7^th Table of Contents
13. 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

10.

Reading Reference: GOB McMurry 7^th 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 7^th 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: http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/nomen1.htm

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:

http://chemed.chem.purdue.edu/genchem/topicreview/bp/1organic/organic.html

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

C₅H₁₂and C₄H₁₀5 total isomers between the two aliphatic alkanes

Test Item #2

C₄H₉Br 4 isomers (alkyl halides)

C₃H₆Br₂ 4 isomers (alkyl dihalides)

Cycloalkanes

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 C_nH_2n. 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
Name	Cyclopropane	Cyclobutane	Cyclopentane	Cyclohexane	Cycloheptane	Cycloalkane
Molecular Formula	C₃H₆	C₄H₈	C₅H₁₀	C₆H₁₂	C₇H₁₄	C_nH_2n
Structural Formula						(CH₂)_n
Line Formula

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:
H₂C=CH– Vinyl group
H₂C=CH–CH₂– Allyl group

C₅H₁₀ 5 total isomers (alkenes only)

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

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

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::