Organic Name :

Functional Group

Alcohol
Group 1 :
Abdurrohman Dzaky Al Hafidz
M. Andika Aryana
Reky Hermawan
Saptio Aji
Suhartini Lestari Putri
Nomenclature

Definition

Classification
Properties

Physical
Properties

Chemical
Properties
Preparation

Alcohols

Impor...
Definition
• Alcohol are compounds in wich a hydroxyl
group (-OH) is attached to a saturated carbon
• The general formula ...
Nomenclature of Alcohols
• IUPAC System
Step 1 : Name the longest chain to which the hydroxyl
group is attached. (alkane –...
Nomenclature of Alcohols
• IUPAC System
Example:
3

2

1

CH3CH2CH2OH
1

2

1-propanol

3

CH3CH2CH2

2-propanol

OH

Alco...
Classification of Alcohols
Monohydric alcohols are classified as primary
(1o), secondary (2o), or tertiary (3o) :
• In pri...
Classification of Alcohols
Example:
primary (1o) : R-CH2-OH
CH3-CH2-CH2-OH 1-propanol (n-propyl alcohol)

secondary (2o): ...
Classification of Alcohols
Example:
tertiary (3o) :

R’’
R-CH-OH
R’

CH3
CH3-CH-OH 2-methyl-2-propanol (t-buthyl alcohol)
...
Physical Properties of Alcohols
• Boiling Points
Alcohol have hinger boiling points than alkanes of
similar molecular weig...
Physical Properties of Alcohols
• Solubility
The polar part of the alcohol molecule increases
solubility in water, but the...
Chemical Properties of Alcohols
1. Reaction with active metals
Alkoxides are formed by Na, Mg, Al etc
H3C-CH2-OH

Na

H3C-...
2. Ester Formation

O
H3C-CH2-OH + H3C-CH2-C-OH
ethanol

propanoic acid

O
H3C-CH2-C-O-CH2-CH3 + H2O
diethyl ester

Alcoho...
3. Dehydration (Reaction with sulphuric acid)
a. Alkene Formation
OH
Conc. H SO
H3C-CH2-CH-CH3
2

4

H3C-CH2-CH=CH2 +

H3C...
3. Dehydration (Reaction with sulphuric acid)
b. Ether Formation
2 H3C-CH2-OH
ethanol

Conc. H2SO4

140o

H3C-CH2-O-CH2-CH...
3. Dehydration (Reaction with sulphuric acid)
c. Alkyl hydrogen sulphates formation
H3C-CH2-OH + HO-SO2OH
ethanol

H3C-CH2...
4. Alkyl halides formation (R-X)
a. Reaction with thionyl chloride (SOCl2)
H3C-CH2-OH + SOCl2
ethanol

H3C-CH2-Cl + SO2 + ...
4. Alkyl halides formation (R-X)
b. Reaction with phosphorus halides (PX3 or PX5)
H3C-CH2-OH + PCl5
ethanol

3 H3C-CH2-OH ...
5. Reaction with hydrogen halides (HX)
HCl react with alcohols only in the presence of catalyst
(anhydrous ZnCl2). No cata...
6. Reaction withnitric acid (HNO3)
alkyl nitrates are formed
H3C-CH2-OH + HBr
ethanol

H3C-CH2-O-NO2 + H2O
ethylnitrate

7...
a) Primary alcohols are oxidized to aldehydes,
which are, in turn, easily axidized to
carboxilic acids. The reaction can b...
b.) secondary alcohol are oxidazed to ketones
O
O
H3C-CH-CH3 +
H3C-C-CH3 + H2O
Isoprophyl alcohol

acetone

c.) Tertiary a...
8. Reaction with hot copper ( catalytic
dehydrogenation)
Different types of alcohols give different
products when their va...
b. ) Secondary alcohols give ketone + hydrogen
OH
O
H3C-C-CH3
H3C-C-CH3 + H2
Isoprophyl alcohol

Acetone

c. ) Tertiary al...
2. Hydration of Alkenes
Alkenes react with conc. H2SO4 to form alkyl hydrogen
sulphates which on hydrolysis yield alcohols...
Bagian OHnya pindah
Keduanya akan berikatan
karena bagian 4OSO3 yang
menjadi H2SO
bermuatan negatif sudah
berikatan dengan...
3. Addition of Reagents to aldehydes and ketones

H+

Ikatan double bond
OMgX akan menjadi
putus. Bagian R akan
OH saat be...
• Primary Alcohols
Obtained by treating Grignard reagents with formaldehyde

H+

Ikatan double bond
putus. Bagian R akan
O...
• Secondary Alcohols
Obtained by treating Grignard reagents with other aldehyde

H+

Ikatan double bond
putus. Bagian R ak...
• Tertiary Alcohols
Obtained by treating Grignard reagents with ketones

H+

Ikatan double bond
putus. Bagian R akan
OMgX ...
5. Reduction of acids with lithium aluminium
hydride (LiAlH4)

Setelah bereaksi
ikatan double
bond dan O
hilang

Alcohols
6. Acid-hydrolysis of esters

Keduanya akan bereaksi
OH akan pindah sehingga
menjadi C3H7OH asam
akan membentuk
asetat

Al...
Important Individual Alcohols
• Methanol (methyl alcohol, wood alcohol). In industry, it is
used as the raw material for m...
Important Individual Alcohols
• 1,2-ethanediol (ethylene glycol) and 1,2- propanediol
(propylenglycol) are components in p...
Thank You
Alcohols
Alcohols
Alcohols
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Alcohols

  1. 1. Organic Name : Functional Group Alcohol
  2. 2. Group 1 : Abdurrohman Dzaky Al Hafidz M. Andika Aryana Reky Hermawan Saptio Aji Suhartini Lestari Putri
  3. 3. Nomenclature Definition Classification Properties Physical Properties Chemical Properties Preparation Alcohols Important Individual Alcohol
  4. 4. Definition • Alcohol are compounds in wich a hydroxyl group (-OH) is attached to a saturated carbon • The general formula of alcohol is ROH (R= alkyl, substitution alkyl, or syclic hidrokarbon) Example: CH3-OH (metanol) CH3CH-OH (etanol) Alcohols
  5. 5. Nomenclature of Alcohols • IUPAC System Step 1 : Name the longest chain to which the hydroxyl group is attached. (alkane –e + ol = Alkanol) Step 2 : Number the longest chain to give the lowest number to the carbon attached to the hydroxyl group Step 3: Indicate the position of the hydroxyl group by the number of the carbon atom to which is attached Step 4: Indicate the position of other substitutients or multiple bonds by number Alcohols
  6. 6. Nomenclature of Alcohols • IUPAC System Example: 3 2 1 CH3CH2CH2OH 1 2 1-propanol 3 CH3CH2CH2 2-propanol OH Alcohols
  7. 7. Classification of Alcohols Monohydric alcohols are classified as primary (1o), secondary (2o), or tertiary (3o) : • In primary (1o) alcohols the –OH is attached to a C atom which is attached to one other • In secondary (2o) alcohols the –OH is attached to a C atom which is attached to two other • In tertiary (3o) alcohols the –OH is attached to a C atom which is attached to three other Alcohols
  8. 8. Classification of Alcohols Example: primary (1o) : R-CH2-OH CH3-CH2-CH2-OH 1-propanol (n-propyl alcohol) secondary (2o): R-CH-OH R’ CH3-CH-OH 2-propanol (isopropyl alcohol) CH3 Alcohols
  9. 9. Classification of Alcohols Example: tertiary (3o) : R’’ R-CH-OH R’ CH3 CH3-CH-OH 2-methyl-2-propanol (t-buthyl alcohol) CH3 Alcohols
  10. 10. Physical Properties of Alcohols • Boiling Points Alcohol have hinger boiling points than alkanes of similar molecular weight. Alcohol boiling points increase as carbon-chain length increases. Example: CH3-OH methyl alcohol BM= 32 oC= 65 CH3-CH2-OH ethyl alcohol BM= 46 oC= 78 CH3-CH2-CH2-OH n-propyl alcohol BM= 60 oC= 97 Alcohols
  11. 11. Physical Properties of Alcohols • Solubility The polar part of the alcohol molecule increases solubility in water, but the non polar part decrease solubility. Size of the non polar alkyl group is large the solubility of alcohol in water decrease dramatically Alcohols
  12. 12. Chemical Properties of Alcohols 1. Reaction with active metals Alkoxides are formed by Na, Mg, Al etc H3C-CH2-OH Na H3C-CH2-ONa Sodium ethoxide Alcohols
  13. 13. 2. Ester Formation O H3C-CH2-OH + H3C-CH2-C-OH ethanol propanoic acid O H3C-CH2-C-O-CH2-CH3 + H2O diethyl ester Alcohols
  14. 14. 3. Dehydration (Reaction with sulphuric acid) a. Alkene Formation OH Conc. H SO H3C-CH2-CH-CH3 2 4 H3C-CH2-CH=CH2 + H3C-CH=CH-CH3 2-butene Major Product Alcohols 1-butene Minor Product
  15. 15. 3. Dehydration (Reaction with sulphuric acid) b. Ether Formation 2 H3C-CH2-OH ethanol Conc. H2SO4 140o H3C-CH2-O-CH2-CH3 H O + 2 diethyl ether Alcohols
  16. 16. 3. Dehydration (Reaction with sulphuric acid) c. Alkyl hydrogen sulphates formation H3C-CH2-OH + HO-SO2OH ethanol H3C-CH2-O-SO2OH + H2O Ethyl hydrogen sulphate Alcohols room temperature
  17. 17. 4. Alkyl halides formation (R-X) a. Reaction with thionyl chloride (SOCl2) H3C-CH2-OH + SOCl2 ethanol H3C-CH2-Cl + SO2 + HCl Ethyl chloride Alcohols
  18. 18. 4. Alkyl halides formation (R-X) b. Reaction with phosphorus halides (PX3 or PX5) H3C-CH2-OH + PCl5 ethanol 3 H3C-CH2-OH + PCl3 ethanol H3C-CH2-Cl + POCl3 + HCl Ethyl chloride H3C-CH2-Cl + H3PO3 Ethyl chloride Alcohols
  19. 19. 5. Reaction with hydrogen halides (HX) HCl react with alcohols only in the presence of catalyst (anhydrous ZnCl2). No catalyst is required in the case of HBr or HI H3C-CH2-OH + HBr ethanol H3C-CH2-Br + H2O Ethyl bromide Alcohols
  20. 20. 6. Reaction withnitric acid (HNO3) alkyl nitrates are formed H3C-CH2-OH + HBr ethanol H3C-CH2-O-NO2 + H2O ethylnitrate 7. Oxydation Different types of alcohols give different products on oxidation. Most widely used oxidizing agents are KMnO4 + H2SO4 and Na2Cr2O7 + H2SO4 Alcohols
  21. 21. a) Primary alcohols are oxidized to aldehydes, which are, in turn, easily axidized to carboxilic acids. The reaction can be stoped at the aldehyde stage, by removing them from the oxidizing medium as they are farmed (e.g. Destilation) O H3C-CH2-OH + Ethylalcohol O H3C-C-H acetaldehyde H3C-C-OH aceticacid Alcohols
  22. 22. b.) secondary alcohol are oxidazed to ketones O O H3C-CH-CH3 + H3C-C-CH3 + H2O Isoprophyl alcohol acetone c.) Tertiary alcohol don’t undergo oxidation under normal condition. OH H3C-C-CH3 + NO REACTION (NR) CH3 Tert-buthyl alcohol Alcohols
  23. 23. 8. Reaction with hot copper ( catalytic dehydrogenation) Different types of alcohols give different products when their vapours are passed over copper gauze at 3000C a) Primary alcohols give aldehydes + hydrogen O H3C-CH2-OH H3C-C-H + H2 Ethylalcohol Acetaldehyde Alcohols
  24. 24. b. ) Secondary alcohols give ketone + hydrogen OH O H3C-C-CH3 H3C-C-CH3 + H2 Isoprophyl alcohol Acetone c. ) Tertiary alcohols give alkenes + water OH CH2 H3C-C-CH3 H3C-C + H2O CH3 CH3 Tert-butyl alcohol 2-methyl propene Alcohols
  25. 25. 2. Hydration of Alkenes Alkenes react with conc. H2SO4 to form alkyl hydrogen sulphates which on hydrolysis yield alcohols Sesuai hukum Markovnikov maka bagian positifnya akan menuju ke bagian C yang Hnya paling banyak Alcohols
  26. 26. Bagian OHnya pindah Keduanya akan berikatan karena bagian 4OSO3 yang menjadi H2SO bermuatan negatif sudah berikatan dengan H Alcohols
  27. 27. 3. Addition of Reagents to aldehydes and ketones H+ Ikatan double bond OMgX akan menjadi putus. Bagian R akan OH saat bereaksi pindah ke C. Bagian MgX akan pindah ke O Alcohols
  28. 28. • Primary Alcohols Obtained by treating Grignard reagents with formaldehyde H+ Ikatan double bond putus. Bagian R akan OMgX akan menjadi pindah ke C. Bagian OH saat bereaksi MgX akan pindah ke O Alcohols
  29. 29. • Secondary Alcohols Obtained by treating Grignard reagents with other aldehyde H+ Ikatan double bond putus. Bagian R akan OMgX akan menjadi pindah ke C. Bagian OH saat bereaksi MgX akan pindah ke O Alcohols
  30. 30. • Tertiary Alcohols Obtained by treating Grignard reagents with ketones H+ Ikatan double bond putus. Bagian R akan OMgX akan menjadi pindah ke C. Bagian OH saat bereaksi MgX akan pindah ke O Alcohols
  31. 31. 5. Reduction of acids with lithium aluminium hydride (LiAlH4) Setelah bereaksi ikatan double bond dan O hilang Alcohols
  32. 32. 6. Acid-hydrolysis of esters Keduanya akan bereaksi OH akan pindah sehingga menjadi C3H7OH asam akan membentuk asetat Alcohols
  33. 33. Important Individual Alcohols • Methanol (methyl alcohol, wood alcohol). In industry, it is used as the raw material for making formaldehyde, as a solvent, and as a denaturant. • Ethanol (ethyl alcohol, grain alcohol). In industry ethanol is used as a solvent and to prepare perfumes, lotions, and rubbing compound. • 2-propanol (isopropyl alcohol) otu used as a disinfectant Alcohols
  34. 34. Important Individual Alcohols • 1,2-ethanediol (ethylene glycol) and 1,2- propanediol (propylenglycol) are components in permanent type antifreezes. • 1,2,3-propanetriol (glycerol, glycerin) it used as afood additive to help keep food moist • Sugars. All carbohydrates consist of polyhydroxy compounds Alcohols
  35. 35. Thank You
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