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Chapter 4

Chapter 4

Alcohols and Alkyl Halides

Alcohols and Alkyl Halides

(1) alcohol + hydrogen halide (1) alcohol + hydrogen halide

ROH + HX

ROH + HX AEAERX + HRX + H22OO

(2) alkane + halogen (2) alkane + halogen

RH + X

RH + X22AEAERX + HXRX + HX

Both are substitution reactions

Both are substitution reactionsOverview of Chapter

Overview of Chapter

This chapter introduces chemical reactions and

This chapter introduces chemical reactions and

their mechanisms by focusing on two reactions their mechanisms by focusing on two reactions that yield alkyl halides. that yield alkyl halides. 4.1 4.1

IUPAC Nomenclature

IUPAC Nomenclature

of Alkyl Halides of Alkyl Halides

The two that are most widely used are:

The two that are most widely used are:

functional class nomenclature functional class nomenclature substitutive nomenclature substitutive nomenclature

Both types can be applied to alcohols and

Both types can be applied to alcohols and

alkyl halides. alkyl halides.IUPAC Nomenclature

IUPAC Nomenclature

There are several kinds of IUPAC nomenclature.

There are several kinds of IUPAC nomenclature.

Name the alkyl group and the halogen as

Name the alkyl group and the halogen as

separate words ( separate words (alkylalkyl+ + halidehalide))Functional Class Nomenclature of Alkyl Halides

Functional Class Nomenclature of Alkyl Halides

CH

CH33FFCHCH33CHCH22CHCH22CHCH22CHCH22ClCl

CH

CH33CHCH22CHCHCHCH22CHCH22CHCH33Br

BrH H I I

Name the alkyl group and the halogen as

Name the alkyl group and the halogen as

separate words ( separate words (alkylalkyl+ + halidehalide))Functional Class Nomenclature of Alkyl Halides

Functional Class Nomenclature of Alkyl Halides

CH

CH33FFCHCH33CHCH22CHCH22CHCH22CHCH22ClCl

CH

CH33CHCH22CHCHCHCH22CHCH22CHCH33Br

BrMethyl fluoride

Methyl fluoridePentyl chloridePentyl chloride

1

1--Ethylhexyl bromideEthylhexyl bromideCyclohexyl iodideCyclohexyl iodideH

H I I

Name as halo

Name as halo--substituted alkanes.substituted alkanes.

Number the longest chain containing the

Number the longest chain containing the

halogen in the direction that gives the lowest halogen in the direction that gives the lowest number to the substituted carbon. number to the substituted carbon.Substitutive Nomenclature of Alkyl Halides

Substitutive Nomenclature of Alkyl Halides

CH Br CH

CH33CHCH22CHCHCHCH22CHCH33I

I

Name as halo

Name as halo--substituted alkanes.substituted alkanes.

Number the longest chain containing the

Number the longest chain containing the

halogen in the direction that gives the lowest halogen in the direction that gives the lowest number to the substituted carbon. number to the substituted carbon.Substitutive Nomenclature of Alkyl Halides

Substitutive Nomenclature of Alkyl Halides

CH

Br11--FluoropentaneFluoropentane

3

3--IodopentaneIodopentane2

I

Substitutive Nomenclature of Alkyl Halides

Substitutive Nomenclature of Alkyl Halides

Halogen and alkyl groups

Halogen and alkyl groups

are of equal rank when are of equal rank when it comes to numbering it comes to numbering the chain. the chain.

Number the chain in the

Number the chain in the

direction that gives the direction that gives the lowest number to the lowest number to the group (halogen or alkyl) group (halogen or alkyl) that appears first. that appears first. CH

CH33Cl

Cl Cl ClCH CH33

Substitutive Nomenclature of Alkyl Halides

Substitutive Nomenclature of Alkyl Halides

5 2 CH

CH33Cl

Cl Cl ClCH CH33 4.2 4.2

IUPAC Nomenclature

IUPAC Nomenclature

of Alcohols of Alcohols

Name the alkyl group and add "alcohol" as a

Name the alkyl group and add "alcohol" as a

separate word. separate word.Functional Class Nomenclature of Alcohols

Functional Class Nomenclature of Alcohols

CH

CH33CHCH22OHOH

CH

CH33CHCHCHCH22CHCH22CHCH22CHCH33OH

OHCH

CH33CCHCCH22CHCH22CHCH33OH

OHCH CH33

Name the alkyl group and add "alcohol" as a

Name the alkyl group and add "alcohol" as a

separate word. separate word.Functional Class Nomenclature of Alcohols

Functional Class Nomenclature of Alcohols

CH

CH33CHCH22OHOH

CH

CH33CHCHCHCH22CHCH22CHCH22CHCH33OH

OHCH

CH33CCHCCH22CHCH22CHCH33OH

OHCH CH33

Ethyl alcohol

Ethyl alcohol

1

1--Methylpentyl alcoholMethylpentyl alcohol1,1

1,1--DimethylbutylDimethylbutyl

alcohol alcohol

Name as "alkanols." Replace

Name as "alkanols." Replace --e ending of alkanee ending of alkane name by name by --ol.ol. Number chain in direction that gives lowest number Number chain in direction that gives lowest number to the carbon that bears the to the carbon that bears the - - OH group.OH group.Substitutive Nomenclature of Alcohols

Substitutive Nomenclature of Alcohols

CH

CH33CHCH22OHOH

CH

CH33CHCHCHCH22CHCH22CHCH22CHCH33OH

OHCH

CH33CCHCCH22CHCH22CHCH33OH

OHCH CH33

Name as "alkanols." Replace

Name as "alkanols." Replace --e ending of alkanee ending of alkane name by name by --ol.ol. Number chain in direction that gives lowest number Number chain in direction that gives lowest number to the carbon that bears the to the carbon that bears the - - OH group.OH group.Substitutive Nomenclature of Alcohols

Substitutive Nomenclature of Alcohols

CH

CH33CHCH22OHOH

CH

CH33CHCHCHCH22CHCH22CHCH22CHCH33OH

OHCH

CH33CCHCCH22CHCH22CHCH33OH

OHCH CH33

Ethanol

Ethanol

2

2--HexanolHexanol2

2--MethylMethyl--22--pentanolpentanol

OH OHCH

CH33Substitutive Nomenclature of Alcohols

Substitutive Nomenclature of Alcohols

Hydroxyl groups outrank

Hydroxyl groups outrank

alkyl groups when alkyl groups when it comes to numbering it comes to numbering the chain. the chain.

Number the chain in the

Number the chain in the

direction that gives the direction that gives the lowest number to the lowest number to the carbon that bears the carbon that bears the

OH group

OH group

CH

CH33OH

OH

Substitutive Nomenclature of Alcohols

Substitutive Nomenclature of Alcohols

6

6--MethylMethyl--33--heptanolheptanol

5

5--MethylMethyl--22--heptanolheptanol

OH OHCH CH33 CH

CH33OH

OH 4.3 4.3

Classes of Alcohols

Classes of Alcohols

and Alkyl Halides and Alkyl Halides

Alcohols and alkyl halides are classified as

Alcohols and alkyl halides are classified as

primary primary secondary secondary tertiary tertiary according to their "degree of substitution." according to their "degree of substitution."

Degree of substitution is determined by counting

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