Module 16 Homework Packet

CHM 1025C Homework Packet Name: __________________

Module 16 Chapter 19: Introduction to Organic Chemistry

A. ______ (02) Alkane Series Section 19.3 Table 19.1 p 445 Answers

B. ______ (02) Alkyl Radicals Section 19.3 Table 19.2 p 449 Answers
C. ______ (08) Structural Isomer Problem Section 19.3 446-450

D. ______ (02) Recognition of 1^o, 2^o, 3^o, 4^o carbons ( 0^o, 1^o, 2^o, 3^o , 4^o) & hydrogen Answers
E. ______ (05) Nomenclature of Alkanes and Cycloalkanes Section 19.3-5 p445-455 Answers
F. ______ (03) Functional Group Recognition Section 19.6 Table 19.4 p460 Answers
_______(22) = ______% Total Chapter 19

Take-Home Lab Part C Structural Isomer Number Problems

______ (01) Structural Isomer Take-Home Problem #1 C₆H₁₄ (makeup-See #7)

______ (04) Structural Isomer Take-Home Problem #2 C₇H₁₆ (makeup C₈H₁₈)

______ (04) Structural Isomer Take-Home Problem #3 C₅H₁₁Br (makeup C₆H₁₃Br)

______ (04) Structural Isomer Take-Home Problem #4 C₄H₈Br₂(makeup C₅H₁₀Br₂)

______ (04) Structural Isomer Take-Home Problem #5 C₆H₁₂ Cycloalkanes only (makeup C₇H₁₄)

______ (04) Structural Isomer Take-Home Problem #6 C₆H₁₂ Alkenes only (makeup C₇H₁₄)

______ (00) Makeup Structural Isomer Take-Home Problem C₄H₁₀O Alcohols & Ethers

________(21) Module 16 Take-Home Lab Total

Foundations of College Chemistry, 14th Edition

Table of Contents

Chapter 19 Introduction to Organic Chemistry 441

19.1 The Beginnings of Organic Chemistry 442

19.2 Why Carbon? 442

19.3 Alkanes 445

19.4 Alkenes and Alkynes 452

19.5 Aromatic Hydrocarbons 456

19.6 Hydrocarbon Derivatives 459

19.7 Alcohols 461

19.8 Ethers 465

19.9 Aldehydes and Ketones 467

19.10 Carboxylic Acids 469

19.11 Esters 471

19.12 Polymers—Macromolecules 473

Review 474

Review Questions, Paired Exercises 477

Additional Exercises 481

Answers to Practice Exercises 482

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.

See Section 19.3 Table 19.1 Page 445

Answers: http://www.lsua.us/chem1001/sampletest/20M16aAnswer.htm

CHM 1025C

Module 16 (Chapter 19) Part B: Alkyl Radicals 2 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

See Table 19.2 Section 19.2 Pages 554-555

Answers: http://www.lsua.us/chem1001/sampletest/20M16bAnswer.htm

Module 16 Part B1: Additional Alkyl and Aryl Radicals 1 bonus point

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 Textbook)

n-pentyl (amyl) isopentyl or isoamyl

neopentyl sec-amyl or sec-pentyl

Allyl vinyl

Benzyl phenyl

o-tolyl m-tolyl p-tolyl

CHM 1025C M-16 Homework Packet

Module 16 (former M-4III) Part C: Structural Isomer Number Problem:

Alkanes, Alkyl halides, and Cycloalkanes 8 points

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

Test Item #1 C₆H₁₄ 5 isomers; 1 point (no Makeup)

Download Real Player and then Download Hexane Isomer Video:

http://www.fccj.info/chem2414/isomers/Hexane_Isomers.rm

Test Item #2 C₅H₁₂and C₄H₁₀5 total isomers between the two alkanes 1 point

See Section 19.2 Guidelines for Drawing Hydrocarbon Isomers Table p553
See Section 19.2 Guidelines for Naming Alkanes p355-6 See Exercise 19.1 p556

Web Page: Structure and Nomenclature of Hydrocarbons:

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

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.

Test Item#3 C₄H₉Br 4 isomers; 1 point (no makeup)

Organic Halides: Reference Section 19.6 Pages 564-565

Directions take four butyl radicals in Part B and replace the X with Bromine and name the alkyl bromides using the IUPAC

Test Item#4 C₃H₆Br₂ 4 isomers; 1 Point (No Makeup)

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.

CHM 1025C M-16 Homework Packet

Test Item #5 C₄H₈ 5 total isomers (cycloalkanes plus alkenes) 1 Point No Makeup

Test Item #6 C₅H₁₀5 isomers (cycloalkanes only); 1 Point (No Makeup)

Test Item #7: C₅H₁₀ 5 isomers (alkenes only) 1 Point (No Makeup)

Reference Section 19.3 pages 557-558

Read Guidelines for Naming Alkenes p557-558 Work Exercise 19.2

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

CHM 1025C M-16 Homework Packet

Test Item #8 C₆H₄Br₂ 3 aromatic isomers 1 Point (No Makeup)

Reference: Section 19.4 Arenes Pages 561-562

CHM 1025C M-16 Homework Packet

Problem #2 C₇H₁₆ 9 isomers (makeup C₈H₁₈) 4 points

Hint: Parent: one heptane; two hexanes; five pentanes; and one butane

CHM 1025C M-16 Homework Packet

Problem #3 C₅H₁₁Br 8 isomers (makeup C₆H₁₃Br) 4 Points

CHM 1025C M-16 Homework Packet

Problem #4: C₄H₈Br₂ 9 isomers (makeup C₅H₁₀Br₂) 4 Points

CHM 1025C M-16 Homework Packet

Problem#5 C₆H₁₂13 isomers (Cycloalkanes only (makeup C₇H₁₄) 4 Points

CHM 1025C M-16 Homework Packet

Problem #6 C₆H₁₂11isomers (alkenes only) (makeup C₇H₁₄) 4 Points

CHM 1025C M-16 Homework Packet

Module 16 Chapter 19 Part D: 2 points

Recognition of 1^o, 2^o, 3^o, 4^o carbons & 1^o, 2^o, 3^o hydrogen

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::