ALCOHOLS p.253

I.  ROH general formula
    R = alkyl an alcohol
    R = aryl a phenol

II. Capable of hydrogen bonding

add methanol to gas tank to tie up any water from freezing

III. Nomenclature
            (1) get parent chain alcohol
                 C-C-C-COH butanol

                                    OH
                                     |
                       C - C - C - C

            (2) give location of OH 2 - butanol

                        Primary, Secondary, Tertiary Alcohols

Primary                                 H
                                    C* - C - OH             The carbon to which the OH is attached is
                                            H                       attached to only hydrogens or one other carbon
                                                                     (3H or 2H & 1C)

Secondary                          C*
                                  C* - C - OH              The carbon to which the OH is attached is also
                                          H                        attached to 2 other carbons (2C 1H)

Tertiary                             C*
                                 C* - C - OH                 The carbon to which the OH is attached is
                                         C*                         attached to 3 carbons (3C no H)

Common Alcohols
                CH₃OH                 methanol or methyl alcohol or wood alcohol

            CH₃-CH₂OH             ethanol - ethyl alcohol - grain alcohol

                    CH₃                 2-propanol - isopropyl alcohol - rubbing alcohol
                CH₃COH
                    H

Draw: ethylene glycol (1,2-ethanediol) and propylene glycol (1,2, propanediol)

                                                        CH₃
                                                          |
                         CH₃ - CH₂ - CH₂ - C - OH
                                                         |
                                                        CH₃

1. count C of parent chain
2. any groups other than OH
3. where is OH
4. where is the methyl group

Is this a 1^o, 2^o, or 3^o alcohol

1. Oxidation

                                    spark
(a) CH₃CH₂OH + 3 O₂ -------> 2 CO₂ + 3 H₂O + Energy

        shish kabob - cherries jubilee
                ignite gunpowder - if the gunpowder burned after the
                alcohol had burned away - "proof" not watered down.
    Denatured alcohol - something toxic is added

                                                            O                                         O
(b) CH₃CH₂CH₂OH ------> CH₃CH₂C - H ------> CH₃CH₂C
                                                                                                        OH
                        1^o                                     aldehyde                         propanoic acid

                    OH                            O
            CH₃CHCH₃ ------> CH₃ C-CH₃

                        2^o                         propanone (ketone)

1E alcohol -------> aldehyde -------> acetic acid -------> CO₂ + energy

    CH₃CH₂OH ------> CH₃CHO -------> CH₃COOH ------> CO₂ + ATP

Phenol     another name is carbolic acid - Lister - disinfectant

Phenol coefficient - effectiveness of an antiseptic rated against a 5% phenol solution

CH₃CH₂OH + H Br -----> CH₃CH₂Br + H₂O

Dehydration* Reaction

    H   OH                        H       H
    |      |                             |         |
HC-CH + H₂SO₄ -----> HC = CH + H₂SO₄ + H₂O
   H    H                             alkene

Acid + alcohol -----> ester + water

acetic acid methyl alcohol methyl acetate ester

butyric acid ethyl alcohol ethyl butyrate ester (strawberry)

Draw

t-butanol 2,3-dimethyl 4-pentanol 2-methyl-2-hexanol

Draw and name a primary, secondary and tertiary 6 carbon alcohol

ALDEHYDES p. 258 Hasta' Have a H

Aldehyde ending is "al" in the official IUPAC nomenclature. For many everyday usages, aldehyde is put in the name.

                H
          H -C = O                                     methanal                         formaldehyde*

                H H
          H -C - C = O                              ethanal                             acetaldehyde*
                H

                                                              propanal                          propionaldehyde

                                                              butanal                            butyraldehyde

* memorize

Naming aldehydes

                                H
                   C - C - C =O
                          |
                         CH₃

1. Find parent chain and add 'al '. propanal

2. Find number and position of groups. 2-methyl-propanal

Do we have to give the position of the aldehyde group? No. It will always be at the end of the chain. An aldehyde has to have a double bond O and one H attached to the Carbon. There's only one bond left. It can be to a H (formaldehyde) or to another carbon which can be part of a chain.

Are propanol and propanal isomers? Draw them out and count the C's, H's, and O's.

KETONES p. 258

Ketones end in 'one' for the official naming. For everyday usage 'ketone' is also used.

                    O
         *
C - C- C- C - C

1. Find parent chain and add 'one'                 pentanone

2. Find where the ketone group =O is.                 2-pentanone

Are pentanone and pentenal isomers?

Draw 3-propyl-1-cyclopentanone.

Additional method of naming ketones

                      O
                 *
    C- C- C - C

1. 'Retangle-u-late the C=O

2. Circle the two other groups and name then

3. Add ketone for the C=O group

    Ethyl methyl ketone

Draw diethyl ketone. How many carbons are in diethyl ketone? 4 or 5?

A. Reduction - add H to the =O and get an alcohol.

Aldehydes -----> 1E alcohol

    propanal     ------->     n-propanol

Ketones -----> 2E alcohol

    propanone     ------>     2-propanol                 Propanone is also known as acetone & dimethyl ketone.
                                                                            2-propanol is also known as isopropyl alcohol.

                                                                                                        reduced
Aldehydes get reduced to 1E alcohols.                             aldehyde ------------> 1E alcohol
                                                                                                       <---------
E1 alcohols get oxidized to aldehydes.                                              oxidized

ACIDS p. 260

Acids end in 'oic acid' for the official naming. Many of the acids have trivial or common usage names. The acid group is -COOH, also called carboxyl group. This class of compounds is also called carboxylic acids.

        HCOOH                                     Methanolic acid                     Formic acid*

        CH₃COOH                                           Ethanoic acid                        Acetic acid*

        CH₃(CH₂)₂COOH                      Butanoic acid                        Butryic acid

        CH₃(CH₂)₁₄COOH                     Hexanoic acid                      Palmitic acid (a fatty acid)

* Memorize

Name

                        Br
                         |
    C - C - C - C - C OOH

The carbon of COOH is always carbon number 1. The bromine is on the 2 position. Another way of naming the carbons away from the COOH is to use the Greek system. Carbon #2 is the alpha or α, carbon #3 is the beta or β.

Since these are acids, they can react with bases to form salts and water.

HCl             +             NaOH     ------------>     Na ⁺Cl ^-     +             H₂O
Hydrochloric acid     Sodium hydroxide             Sodium chloride             water

    OH                                                                        O  ^-Na⁺
      |                                                                             |
CH₃C=O     +             NaOH     --------------> CH₃C=O     +     H₂O

Acetic acid Sodium hydroxide Sodium acetate water

When acids form salts, the salt ending is 'ate'. Draw sodium butyrate.

Common Acids

Benzoic acid                                                   Food preservative
                                                                      Manufacture of dyes, cosmetics, plastics
                                                                      p-aminobenzoic acid (PABA)

Citric acid                                                      Flavoring for candy, soft drinks
                                                                     Anticoagulant

Salicylic acid o-hydroxybenzoic acid Acetosalicylic acid - Aspirin

Reactions of acids

        The acid group gets reduced to an aldehyde.

                                 OH                                        H
                                   |                                            |
                    CH₃CH₂C=O ------------> CH₃CH₂C=O

                        oxidized                     oxidized
    1E alcohol ------------> aldehyde ------------> acid
                    <----------                   <----------
                       reduced                         reduced

            Acid     +     Alcohol     ---------->     Ester     +     Water

                      O
            H   *                             H                                 H   H         H
        H C - C- OH     +     HO - C - H     ------->     H C - C -O - C - H     +     HOH
            H                                    H                                 H   H         H
        acetic acid                     methanol                             methyl acetate

Circle the H from the alcohol (methanol) and the OH from the acid (acetic acid) to give a HOH (water).

ETHERS p. 256

ROR or C-O-C Two alkyl groups are attached to the same oxygen.

Highly flammable, can form explosive peroxides.

    C-C-O-C-C         diethyl ether        Generally called ether. Was used for anesthetic. 
                                                            Had side effects, no longer used as such.

Methyl propyl ether is Neothyl              Draw it.

                    CH₃                                 methyl ter-butyl ether (MTBE) is added to gasolines to reduce
   CH₃ - O - C - CH₃                                   emission of carbon monoxide and replace tetraethyl lead as the
                    CH₃                                           antiknock additive.

AMINES Chapter 16

Contain carbon, hydrogen, and nitrogen. NH₃ is ammonia. Replacing 1, 2, or all 3 of the hydrogens with alkyl groups gives an amine.
            Basic in nature.

Simpliest amine is CH₃NH₂             methyl amine

Amino acids are the building blocks of proteins

          NH_{2
              |}
        H C - COOH         This is glycine. The simpliest amino acid
          |
         H

                              O
               2
Urea             H₂N-C-NH₂

Monday, February 04, 2008 11:30:04 AM