chapter 13 unsaturated hydrocarbons general, organic, & biological chemistry janice gorzynski...

CHAPTER 13Unsaturated Hydrocarbons

General, Organic, & Biological ChemistryJanice Gorzynski Smith

2

CHAPTER 13: Unsaturated Hydrocarbons

Smith. General Organic & Biolocial Chemistry 2nd Ed.

Learning Objectives:

Identify unsaturated hydrocarbons: alkenes, alkynes,

aromatic compounds

Alkene, Alkyne, Aromatic nomenclature

Stereoisomers

Addition Reactions

Polymers

Substitution Reactions

Functional Groups Overview

3Smith. General Organic & Biolocial Chemistry 2nd Ed.

Alkane

Alkene

Alkyne

Aromatic

C − C

C = C

C = C

HydrocarbonFunctional

Groups

Hydrocarbon Chemical formulas


Alkane

Alkene

Alkyne

Aromatic

C − C

C = C

C = C

CnH2n+2 if a chain

CnH2n if a cycloalkane

CnH2n if a chain with 1 dbl bond

CnH2n-2 if a cycloalkene with 1 dbl

bond

CnH2n-2if a chain with 1 triple bond

C6H6

5

Molecule Shape Drawing Alkenes


SIMPLIFY!

C CCCH HHH

H HHHH

CH3CH2CH2=CH2

..

6

Nomenclature Alkanes

#Greek Root

Straight Chain Alkane Name

1 meth methane2 eth ethane3 prop propane4 but butane5 pent pentane6 hex hexane7 hept heptane8 oct octane9 non nonane

10 dec decane

# Carbons Structure

Alkyl Group Name

1 CH3- methyl2 CH3CH2- ethyl3 CH3CH2CH2- propyl4 CH3CH2CH2CH2- butyl5 CH3CH2CH2CH2CH2- pentyl6 CH3CH2CH2CH2CH2CH2- hexyl


parent suffixprefix + +

prefix

parent

suffix

What, where are the substituents?Example: 2,4- dimethyl

How many carbons in longest chain?Example: hex

What is the functional group?Example: ane

2,4-dimethylhexane

12

34

5

6

7

Nomenclature Alkenes & Alkynes

#Greek Root



10 dec decane

# Carbons Structure

Alkyl Group Name




prefix

parent

suffix

First give location and type of substituentsSecond give location of double bond

How many carbons in longest chain?

How many of the functional group and what is it? Alkene = ene; Alkyne = yne

hexa

12

34

5

6

diene2,4-dimethyl 1,5-* Note: when we have more then 1 multiple bond the parent name has an “a” added on: hexa instead of hex

8


#Greek Root



10 dec decane

# Carbons Structure

Alkyl Group Name



prefix

parent

suffix




pent yne4-methyl 2-


123

4

5

9


#Greek Root



10 dec decane

# Carbons Structure

Alkyl Group Name



prefix

parent

suffix




pent ene3-methyl 1-


12

3

4

5

cyclo

10

Nomenclature Aromatics: Benzene


prefix

parent

Give location, number, and type of substituent. You can also replace location & number with o, m, p

“Benzene”

benzene1,2-dimethyl

parentprefix +

1

2

3

4

5 6

benzeneo-dimethyl

o -

m -

p -

Polysubstituted Benzenes:1. Number to give lowest #s around ring2. Alphabetize substituents3. If part of common root name the

molecule as a derivative of a monosubstituted benzene with common root at C1.

11

GroupProblem

Practice naming Alkenes & Alkynes!

Bond Angles Alkenes & Alkynes

ethylene

acetylene

120°

180°

Alkenes Stereoisomers

R

R

R RCIS TRANS


Linoleic Acid


StereoisomersDifferent 3-D shape

Same bonds

ConformationalIsomers

Different bonds between atoms

Alkene Reactions Addition

Addition Rxns: when elements are added to a compound

X Y

X Y

Alkene Reactions Addition

H H

H

H

X

OH

XX

H2

Metal catalyst

Hydrogenation

X2

X = Cl or Br

Halogenation

HX

X = Cl or Br

Hydrohalogenation

H2O

H2SO4

Hydration


Nucleophile vs Electrophile

Alkene Reactions Polymers

Polymerization: joining together of monomers

Aromatic Reactions Substitution

Substitution Rxns: when an atom is replaced by another atom or group of atoms

X Y

H X

YH

Aromatic Reactions Substitution

Cl2Clorination

HNO3

H2SO4

Nitration

SO3

H2SO4

Sulfonation

H

SO3H

NO2

Cl

chapter 13 unsaturated hydrocarbons general, organic, & biological chemistry janice gorzynski...

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