9 2 Substituted Hydrocarbons The electric drill can

9. 2 Substituted Hydrocarbons The electric drill can be used to drill holes, tighten a screw, or sand a rough surface. To change the function of the drill, you replace, or substitute, an attachment. twist drill bit Forstner drill bit hole saw bit drum sander Phillips screwdriver bit

9. 2 Substituted Hydrocarbons A carbon atom in an organic compound can have four attachments. • In a methane molecule, the carbon atom has four identical attachments—its hydrogen atoms. • Chlorine atoms can replace hydrogen atoms. CH 4 + Cl 2 CH 3 Cl + HCl

9. 2 Substituted Hydrocarbons Chloromethane and hydrogen chloride are products of the reaction between methane and chlorine. Other products have two, three, or four chlorine atoms. Organic compounds containing chlorine or other halogens are halocarbons.

9. 2 Substituted Hydrocarbons A hydrocarbon in which one or more hydrogen atoms have been replaced by an atom or group of atoms is a substituted hydrocarbon. The substituted atom or group of atoms is called a functional group.

9. 2 Substituted Hydrocarbons Exploring Boiling Points of Chlorocarbons Graph the data below, plotting boiling point vs. number of chlorine atoms. Draw a smooth curve connecting the points.

9. 2 Substituted Hydrocarbons Exploring Boiling Points of Chlorocarbons

9. 2 Substituted Hydrocarbons Exploring Boiling Points of Chlorocarbons 1. Using Graphs Predict the boiling point of dichloromethane.

9. 2 Substituted Hydrocarbons Exploring Boiling Points of Chlorocarbons 1. Using Graphs Predict the boiling point of dichloromethane. Answer: The boiling point of dichloromethane is 40°C, but temperatures between – 24°C and 61°C are acceptable.

9. 2 Substituted Hydrocarbons Exploring Boiling Points of Chlorocarbons 2. Relating Cause and Effect What effect does increasing the number of chlorine atoms have on the boiling point?

9. 2 Substituted Hydrocarbons Exploring Boiling Points of Chlorocarbons 2. Relating Cause and Effect What effect does increasing the number of chlorine atoms have on the boiling point? Answer: As the number of chlorine atoms increases, the boiling point increases.

9. 2 Substituted Hydrocarbons Exploring Boiling Points of Chlorocarbons 3. Formulating Hypotheses Why is the boiling point of CH 3 Br higher than the boiling point of CH 3 Cl? (Hint: Compare the atomic masses for bromine and chlorine. )

9. 2 Substituted Hydrocarbons Exploring Boiling Points of Chlorocarbons 3. Formulating Hypotheses Why is the boiling point of CH 3 Br higher than the boiling point of CH 3 Cl? (Hint: Compare the atomic masses for bromine and chlorine. ) Answer: Bromine is more massive than chlorine.

9. 2 Substituted Hydrocarbons Alcohols What functional groups are found in alcohols? The functional group in an alcohol is a hydroxyl group, –OH.

9. 2 Substituted Hydrocarbons Alcohols Methanol and ethanol are alcohols. • Methanol, CH 3 OH, is used as a fuel in some motorcycles. • Ethanol, CH 3 CH 2 OH, is often mixed with gasoline to help the gasoline burn more completely. • The name of an alcohol ends in –ol.

9. 2 Substituted Hydrocarbons Alcohols When a halocarbon reacts with a base, the products are an alcohol and salt. CH 3 Cl + Na. OH CH 3 OH + Na. Cl An alcohol can also be made by reacting an alkene with water.

9. 2 Substituted Hydrocarbons Organic Acids and Bases What functional groups are found in organic acids and organic bases? The functional group in organic acids is a carboxyl group, –COOH. The functional group in an amine is an amino group, –NH 2.

9. 2 Substituted Hydrocarbons Organic Acids and Bases The names of organic acids end in -oic. Organic acids tend to have sharp tastes and strong odors. The sharp, sour taste of a lemon comes from citric acid, an organic acid. The simplest organic acid is methanoic acid. Vinegar is a solution of water and ethanoic acid (also known as acetic acid).

9. 2 Substituted Hydrocarbons Organic Acids and Bases Birds sometimes will sit on an ants’ nest and allow the ants to crawl over them. The methanoic acid sprayed by the ants is a natural pesticide that kills mites in the birds’ feathers.

9. 2 Substituted Hydrocarbons Organic Acids and Bases Do you know the smell of rotten fish? Then you’ve encountered a type of substituted hydrocarbon called an amine. Amines are organic bases. Amines are found in paints, dyes, and disinfectants.

9. 2 Substituted Hydrocarbons Esters How are esters formed? Esters form when organic acids react with alcohols.

9. 2 Substituted Hydrocarbons Esters are a group of substituted hydrocarbons. Esters form when organic acids react with alcohols. In a reversible reaction, ethanoic acid and methanol produce methyl ethanoate (methyl acetate).

9. 2 Substituted Hydrocarbons Esters are used in many processed foods to produce fruit flavors. Esters in roses and other flowers have distinctive odors that attract insects.

9. 2 Substituted Hydrocarbons Assessment Questions 1. An alcohol is formed by replacing at least one hydrogen in a hydrocarbon with a(n) a. b. c. d. carboxyl group. hydroxyl group. amino group. carbon group.

9. 2 Substituted Hydrocarbons Assessment Questions 1. An alcohol is formed by replacing at least one hydrogen in a hydrocarbon with a(n) a. b. c. d. carboxyl group. hydroxyl group. amino group. carbon group. ANS: B

9. 2 Substituted Hydrocarbons Assessment Questions 2. What are the products of the reaction between chloroethane and sodium hydroxide? a. b. c. d. ethanoic acid and sodium chloride ethanol and sodium chloride sodium ethanoate and chlorine chloroethanol and sodium

9. 2 Substituted Hydrocarbons Assessment Questions 2. What are the products of the reaction between chloroethane and sodium hydroxide? a. b. c. d. ethanoic acid and sodium chloride ethanol and sodium chloride sodium ethanoate and chlorine chloroethanol and sodium ANS: B