Chapter 13 Alcohols and Phenols
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1 Chapter 13 Alcohols and Phenols
2 Alcohols and Phenols Structure and Physical Properties
3 Alcohols, Ethers, Phenols Structure of Functional Groups
4 Alcohols, Ethers, Phenols Structure of Functional Groups
5 Alcohols, Ethers, Phenols Structure of Functional Groups In water, the -- bond angle is due to repulsion of the bonding electron pairs by the larger non-bonding electron pairs. In alcohols, phenols, and ethers the corresponding bond angles are closer to the expected tetrahedral due to the replacement of one or both hydrogen atoms by larger carbon atoms.
6 Common Names of Alcohols
7 Isomerism in Alcohols 1-propanol 2-propanol
8 Subclassification of Alcohols
9 Subclassification of Alcohols
10 Subclassification of Alcohols
11 Alcohols Nomenclature
12 Nomenclature of Alcohols closest to the
13 Nomenclature of Alcohols
14 A 2-heptanol B 2-methyl-2-propanol C 2,2-dimethyl-1-propanol D 2-ethyl-3-methyl-1-butanol E 2-ethyl-5-methyl-cyclohexanol
15 Alcohols and Phenols Physical Properties
16 Physical Properties of Alcohols Boiling points increase with molecular weight and decrease with branching. Boiling points are higher than alkanes of similar molecular weight. 3 C 3 C 3 C 3 C 3 C 3 C 3 C 3 C 3 C 3 C C 3 C 3 C 3 C 3 C 3 ctane, boiling point = 126 C Attractive forces between alkane molecules are limited to simple London forces. eptanol, boiling point = 176 C Attractive forces between alcohol molecules include both dispersion forces and relatively strong hydrogen bonding.
17 Physical Properties of Alcohols
18 Physical Properties of Alcohols Alcohols are more water soluble than alkanes, but their water solubility is limited by the size of the nonpolar portion of the molecule. Nonpolar, or hydrophobic portions of molecules C 3 Polar, or hydrophilic portions of molecules 3 C C2
19 Physical Properties of Alcohols-Solubility
20 Physical Properties of Alcohols-Solubility C 3 C 3 TE RELATIVELY SMALL ATTRACTIN BETWEEN METANL MLECULES MAKES IT EASY FR WATER T SEPARATE INDIVIDUAL METANL MLECULES FRM EAC TER AND DISSLVE TE ALCL. METANL IS VERY SLUBLE IN WATER. TE RELATIVELY LARGE ATTRACTIN BETWEEN EPTANL MLECULES MAKES IT DIFFICULT FR WATER T SEPARATE INDIVIDUAL EPTANL MLECULES FRM EAC TER AND DISSLVE TE ALCL. EPTANL IS VERY SLIGTLY SLUBLE IN WATER. 3 C C2 3 C C2
21 Alcohols and Phenols Acidity
22 Short pka Table Functional group Example pka Acid Strength Conjugate base Base strength 3 C C Cl Mineral Acid -8 Carboxylic Acid Phenol Ar 10 5 Ar 3 C Cl C Alcohol Alkyl 16 Alkyl Alkyne R C C 25 Amine ~35 R N R C C R N Alkane R C ~50 R C
23 Alcohols - Acidity
24 Alkoxide Salts Formed by an xidation-reduction Reaction Na 3 C Na 3 C 2 3 C Na + 2 Na 3 C Na 3 C
25 Phenols - Structure General Structure - A hydroxyl () group attached directly to an aromatic ring: Phenol α-naphthol β-naphthol Note: C2 is not a phenol.
26 Phenols - Nomenclature Phenols are named as aromatic compounds, using the ortho-, meta-, and para- prefixes or appropriate numbering. 1 N nitrophenol or ortho-nitrophenol Cl 3-chlorophenol or meta-chlorophenol C3 4-methylphenol or para-methylphenol 1 Br 1 2,4-dibromophenol Br 2 Cl Br 4-bromo-2-chloro-5-isopropyl-phenol
27 Phenols - Physical Properties Low Melting Solids Soluble in Nonpolar Solvents Also, Quite soluble in Water Name Phenol Catechol Resorcinol M.P ºC 105 ºC 110 ºC Solubility 8.3 g/100ml 43 g/100ml 110 g/100ml in water
28 Phenols - Acidity In water, phenol dissociates slightly as a weak acid. (Another name for phenol itself is carbolic acid ) _ Acid Base Base Acid
29 Phenols - Acidity ow acidic is Phenol? pka = A general measure of acidity. The lower the pka, the stronger the acid.!! Compound pka nonacids weak acids strong acids Methanol 16 Water 15.7 Phenol 9.9 Acetic Acid 4.8 Phosphoric Acid -2.1 ydrochloric Acid -7
30 pka=18 pka=10 pka=10.5 pka=9.2 N 2 Cl pka=10.3 pka=7.2 C 3 N pka=10.2 N pka=4.1 C 3 N pka=10 N N pka=0.3 N
31
32 Phenols - Chemical Properties Acid-Base Reactions - Na + + Na + xidation- Reduction Reactions Phenol XIDATIN Sodium phenoxide + 2. ydroquinone REDUCTIN Paraquinone
33 Phenols - Examples of Important Compounds C2C2C2C2C2C3 o-phenyl phenol n-hexylresorcinol C 3 butylated hydroxy anisole (BA) C3 butylated hydroxy toluene (BT)
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