Chapter 12 Study Pack

Path 4 Chapter 12 Study Pack Name: __________________

Chapter 12: Introduction to Organic Chemistry

A. ______ Alkane Series Table 19.1 p 445 Answers

B. ______ Alkyl Radicals Table 19.2 p 449 Answers
C. ______ Structural Isomer Problem Section

D. ______ Recognition of 1^o, 2^o, 3^o, 4^o carbons ( 0^o, 1^o, 2^o, 3^o , 4^o) & hydrogen Answers
E. ______ Nomenclature of Alkanes and Cycloalkanes Answers
F. ______ Functional Group Recognition Answers
Chapter 19

In Class/Take-Home Lab Structural Isomer Number Problems

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

______ (03) Structural Isomer Take-Home Problem #2 C₇H₁₆ (makeup C₈H₁₈)

______ (03) Structural Isomer Take-Home Problem #3 C₅H₁₁Br (makeup C₆H₁₃Br)

______ (03) Structural Isomer Take-Home Problem #4 C₄H₈Br₂(makeup C₅H₁₀Br₂)

______ (03) Structural Isomer Take-Home Problem #5 C₆H₁₂ Cycloalkanes only (makeup C₇H₁₄)

______ (03) Structural Isomer Take-Home Problem #6 C₆H₁₂ Alkenes only (makeup C₇H₁₄)

______ (02) Makeup Structural Isomer Take-Home Problem C₄H₁₀O Alcohols & Ethers

________(18) Module 16 Take-Home Lab Total

Conceptual Chemistry 5^th Edition John Suchocki
Table of Contents .

Chapter 20 Organic Compounds

Links to Videos for each Chapter section:

      12.1 Hydrocarbons Contain Only Carbon
      and Hydrogen
      12.2 Unsaturated Hydrocarbons Have
      Multiple Bonds
      12.3 Functional Groups Give Organic
      Compounds Character
      12.4 Alcohols, Phenols, and Ethers
      Contain Oxygen
      12.5 Amines and Alkaloids Contain Nitrogen
      12.6 Carbonyl Containing Compounds
      12.7 An Example of Organic Synthesis
      12.8 Organic Molecules Can Link to
      Form Polymers
      12.9 A Brief History of Plastics

Chapter 12 Part A: Alkane Series

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

Name Chemical Formula

10.

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

CHM 1020 Chapter 12 Study Pack-Part B continued

Chapter 12 Part B: Alkyl Radicals

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

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

Chapter 12 Part B1: Additional Alkyl and Aryl Radicals

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 1020 Chapter 12 Homework Pack

Chapter 12 Part C: Structural Isomer Number Problem:

Alkanes, Alkyl halides, and Cycloalkanes

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;

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

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;

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;

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 1020 Chapter 12 Study Pack-Part C continued

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

Test Item #6 C₅H₁₀5 isomers (cycloalkanes only);

Read Guidelines for Naming Alkenes:

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

Test Item #7: C₅H₁₀ 5 isomers (alkenes only)

Test Item #8 C₆H₄Br₂ 3 aromatic isomers

CHM 1020 Chapter 12 Study Pack-Part C continued

Problem #2 C₇H₁₆ 9 isomers (makeup C₈H₁₈)

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

CHM 1020 Chapter 12 Study Pack-Part C continued

Problem #3 C₅H₁₁Br 8 isomers (makeup C₆H₁₃Br)

CHM 1020 Chapter 12 Study Pack-Part C continued

Problem #4: C₄H₈Br₂ 9 isomers (makeup C₅H₁₀Br₂)

CHM 1020 Chapter 12 Study Pack-Part C continued

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

CHM 1020 Chapter 12 Study Pack-Part C continued

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

CHM 1020 Chapter 12 Study Pack-Part D continued

Chapter 12 Part D:

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::