alk

1. Chapter 4
Alcohols and Alkyl Halides

2. (1) alcohol + hydrogen halide
ROH + HX  RX + H2O
(2) alkane + halogen
RH + X2  RX + HX
Both are substitution reactions
Overview of Chapter
This chapter introduces chemical reactions and
their mechanisms by focusing on two reactions
that yield alkyl halides.

3. 4.1
Functional Groups

4. a structural unit in a molecule responsible for its
characteristic behavior under a particular set of
reaction conditions
Functional Group

5. Alcohol ROH
Alkyl halide RX (X = F, Cl, Br, I)
Amine primary amine: RNH2
secondary amine: R2NH
tertiary amine: R3N
Families of organic compounds
and their functional groups

6. Ether ROR'
Nitrile RCN
Nitroalkane RNO2
Sulfide RSR'
Thiol RSH
Epoxide C C
O
Families of organic compounds
and their functional groups

7. O
C
Carbonyl group
O
C
Acyl group
R
Many classes of organic compounds contain
a carbonyl group

8. O
C
Carbonyl group
O
C
Aldehyde
R H
Many classes of organic compounds contain
a carbonyl group

9. O
C
Carbonyl group
O
C
Ketone
R R'
Many classes of organic compounds contain
a carbonyl group

10. O
C
Carbonyl group
O
C
Carboxylic acid
R OH
Many classes of organic compounds contain
a carbonyl group

11. O
C
Carbonyl group
O
C
Ester
R OR'
Many classes of organic compounds contain
a carbonyl group

12. O
C
Carbonyl group
O
C
Amide
R NH2
Many classes of organic compounds contain
a carbonyl group

13. 4.2
IUPAC Nomenclature
of Alkyl Halides

14. The two that are most widely used are:
functional class nomenclature
substitutive nomenclature
Both types can be applied to alcohols and
alkyl halides.
IUPAC Nomenclature
There are several kinds of IUPAC nomenclature.

15. Name the alkyl group and the halogen as
separate words (alkyl + halide)
Functional Class Nomenclature of Alkyl Halides
CH3F CH3CH2CH2CH2CH2Cl
CH3CH2CHCH2CH2CH3
Br
H
I

16. Name the alkyl group and the halogen as
separate words (alkyl + halide)
Functional Class Nomenclature of Alkyl Halides
CH3F CH3CH2CH2CH2CH2Cl
CH3CH2CHCH2CH2CH3
Br
Methyl fluoride Pentyl chloride
1-Ethylhexyl bromide Cyclohexyl iodide
H
I

17. Name as halo-substituted alkanes.
Number the longest chain containing the
halogen in the direction that gives the lowest
number to the substituted carbon.
Substitutive Nomenclature of Alkyl Halides
CH3CH2CH2CH2CH2F CH3CHCH2CH2CH3
Br
CH3CH2CHCH2CH3
I

18. Name as halo-substituted alkanes.
Number the longest chain containing the
halogen in the direction that gives the lowest
number to the substituted carbon.
Substitutive Nomenclature of Alkyl Halides
CH3CH2CH2CH2CH2F CH3CHCH2CH2CH3
Br
1-Fluoropentane
3-Iodopentane
2-Bromopentane
CH3CH2CHCH2CH3
I

19. Substitutive Nomenclature of Alkyl Halides
Halogen and alkyl groups
are of equal rank when
it comes to numbering
the chain.
Number the chain in the
direction that gives the
lowest number to the
group (halogen or alkyl)
that appears first.
CH3
Cl
Cl
CH3

20. Substitutive Nomenclature of Alkyl Halides
5-Chloro-2-methylheptane
2-Chloro-5-methylheptane
CH3
Cl
Cl
CH3

21. 4.3
IUPAC Nomenclature
of Alcohols

22. Name the alkyl group and add "alcohol" as a
separate word.
Functional Class Nomenclature of Alcohols
CH3CH2OH
CH3CHCH2CH2CH2CH3
OH
CH3CCH2CH2CH3
OH
CH3

23. Name the alkyl group and add "alcohol" as a
separate word.
Functional Class Nomenclature of Alcohols
CH3CH2OH
CH3CHCH2CH2CH2CH3
OH
CH3CCH2CH2CH3
OH
CH3
Ethyl alcohol
1-Methylpentyl alcohol
1,1-Dimethylbutyl
alcohol

24. Name as "alkanols." Replace -e ending of alkane
name by -ol.
Number chain in direction that gives lowest number
to the carbon that bears the —OH group.
Substitutive Nomenclature of Alcohols
CH3CH2OH
CH3CHCH2CH2CH2CH3
OH
CH3CCH2CH2CH3
OH
CH3

25. Name as "alkanols." Replace -e ending of alkane
name by -ol.
Number chain in direction that gives lowest number
to the carbon that bears the —OH group.
Substitutive Nomenclature of Alcohols
CH3CH2OH
CH3CHCH2CH2CH2CH3
OH
CH3CCH2CH2CH3
OH
CH3
Ethanol
2-Hexanol
2-Methyl-2-pentanol

26. OH
CH3
Substitutive Nomenclature of Alcohols
Hydroxyl groups outrank
alkyl groups when
it comes to numbering
the chain.
Number the chain in the
direction that gives the
lowest number to the
carbon that bears the
OH group
CH3
OH

27. Substitutive Nomenclature of Alcohols
6-Methyl-3-heptanol
5-Methyl-2-heptanol
OH
CH3
CH3
OH

28. 4.4
Classes of Alcohols
and Alkyl Halides

29. Alcohols and alkyl halides are classified as
primary
secondary
tertiary
according to their "degree of substitution."
Degree of substitution is determined by counting
the number of carbon atoms directly attached to
the carbon that bears the halogen or hydroxyl group.
Classification

30. CH3CH2CH2CH2CH2F
CH3CHCH2CH2CH3
Br
primary alkyl halide
secondary alkyl halide
Classification
CH3CCH2CH2CH3
OH
CH3
tertiary alcohol
H
OH
secondary alcohol