Organic Reactions. Alcohols and Esterification

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1 Organic Reactions Alcohols and Esterification

2 Alcohols Ex: Ethanol (alcohol in alcoholic beverages) Ethanol production: Fermentation of glucose sugar by yeast cells - C 6 H 12 O 6 (aq) 2C 2 H 5 OH(aq) + 2CO 2 (g) Can be produced industrially through addition reaction: Ethene with steam (water) over acid catalyst Alcohols react by: combustion to form CO 2 and H 2 O (if complete) and CO (if incomplete) oxidation reactions

3 Oxidation Oxidation: Loss of electrons in a chemical process Increase in oxidation number Always accompanied by a reduction 1º alcohols (ex. Ethanol) can be oxidized twice. First oxidation yields aldehyde Can be oxidized again to yield carboxylic acid. Oxidizing agent is an acidified solution of potassium dichromate (H + /K 2 Cr 2 O 7 ). K 2 Cr 2 O 7 is orange in color, and after oxidizes something (been reduced itself), it turns green

4 1º Alcohols Alcohol carbon is attached to one other carbon (1º alcohol) and two reactive hydrogens In the 1 st oxidation: 1 reactive hydrogen removed from the functional group carbon

5 1º Alcohols The aldehyde further oxidized (2 nd oxidation) Carbon attached to the functional group still has one reactive hydrogen

6 1º Alcohols Oxidation of alcohol: basis for a type of simple breathalyzer test (detect ethanol in the breath) The subject breathes into a device containing orange colored crystals of acidified potassium dichromate If ethanol is present in the breath, it will be oxidized by the acidified potassium dichromate, turning the crystals to a green color This color change is detected by a photocell, and the level of change is proportional to the amount of alcohol in the breath

7 Distillation Oxidation of 1º alcohols can occur in two steps So, possible to isolate 2 compounds in right conditions If want aldehyde: Distillation used to allow the aldehyde to be removed before the reaction goes further

8 Reflux To collect a carboxylic acid: Aldehyde must be re-oxidized before it is removed from the reaction chamber by using reflux Aldehyde vapor is not allowed to escape from the condenser: it drips back into the flask where it contacts the heated oxidizing agent and is converted into the carboxylic acid

9 2º & 3º Alcohols Secondary alcohols (ex. propan-2-ol) Only undergo one oxidation Carbon attached to the functional group only has one reactive hydrogen Acidified potassium dichromate is a suitable oxidizing agent in this reaction as well Tertiary alcohols are not easily oxidized because the carbon attached to the functional group has no reactive hydrogens:

10 Esterification Alcohols react with Carboxylic Acids to form Esters - Esterification = Condensation Reaction - Removes water to make an ester - Catalyzed by heat and concentrated H 2 SO 4

11 Equilibrium Reaction Esterification

12 Esterification Esters are not able to hydrogen bond, therefore they have a lower boiling point than carboxylic acids and alcohols Can be removed through distillation

13 Esters have distinct smells that can be detected if the reaction mixture is poured into water Esters are immiscible in water and will form a layer on the surface Can be separated with a separation funnel Esterification

14 Nucleophilic Substitution of Halogenoalkanes Electronegativity differences between Carbon and Halogens cause polarity Halogen = partial - Carbon = partial + = electron deficient

15 Nucleophiles: reactants that are electron rich (δ-) Have a lone pair and may also have a - charge Attracted to δ+ electron deficient carbon atom in the halogenoalkane Substitution with halogen = nucleophilic substitution Nucleophiles

16 Nucleophilic Substitution Halogenoalkanes react with alkalis such as NaOH to form alcohols

17 Nucleophiles: reactants that are electron rich (δ-) Have a lone pair and may also have a - charge Attracted to δ+ electron deficient carbon atom in the halogenoalkane Substitution with halogen = nucleophilic substitution Nucleophiles

18 Benzene Benzene has delocalized electrons that give it special stability Addition reactions destabilize the ring and are not favored Substitution reactions occur instead Delocalized ring of electrons represent an area of electron density (the site of reactivity)

19 Electrophilic Substitution of Benzene Electrophiles are reactants that are electron deficient (+ or δ- charge) Attracted to electron rich moleculeslike the benzene ring! Leads to Electrophilic substitution reaction

20 Benzene + NO 2 + H 2 O

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