Chapter 14 Lecture Conceptual Integrated Science Second Edition © 2013 Pearson Education, Inc. Organic Compounds

© 2013 Pearson Education, Inc. This lecture will help you understand: Organic Chemistry Hydrocarbons Unsaturated Hydrocarbons Functional Groups Alcohols, Phenols, and Ethers Amines and Alkaloids Carbonyl Compounds Polymers

© 2013 Pearson Education, Inc. Organic Chemistry Organic chemistry is the branch of chemistry that involves the study of carbon-containing chemical compounds. An organic compound is a carbon-containing chemical compound. More than 13 million organic compounds are known.

© 2013 Pearson Education, Inc. Carbon atoms connect with one another through strong and stable covalent bonds. Organic Chemistry

© 2013 Pearson Education, Inc. CCC C C C NNN N N N OOO O O O SS S SS 347 kJ/mol 159 kJ/mol 138 kJ/mol 226 kJ/mol Organic Chemistry

© 2013 Pearson Education, Inc. Organic Chemistry Carbon atoms also readily form bonds with many other types of atoms. This provides for a nearly infinite number of different kinds of organic compounds.

© 2013 Pearson Education, Inc. Hydrocarbons A hydrocarbon is a chemical compound that contains only hydrogen and carbon.

© 2013 Pearson Education, Inc. Hydrocarbons

© 2013 Pearson Education, Inc. Structural isomers are molecules that have the same molecular formula but different configurations. Hydrocarbons

© 2013 Pearson Education, Inc. A configuration is the specific way in which the atoms of a molecule are connected to one another. "configuration" = "connectivity" Conformation is the spatial orientation of a single configuration. Hydrocarbons

© 2013 Pearson Education, Inc. C 7 H 16 C 8 H 18 C 10 H 22 C 20 H 42 C 6 H 14 C 5 H , Formula Number of possible isomers

© 2013 Pearson Education, Inc. What is the chemical formula for the following structure? A.C 3 H 8 B.C 4 H 10 C.C 5 H 12 D.C 6 H 14 Explain your answer to your neighbor. Hydrocarbons CHECK YOUR NEIGHBOR c c c c c H H H HH H H H H H H H

© 2013 Pearson Education, Inc. What is the chemical formula for the following structure? A.C 3 H 8 B.C 4 H 10 C.C 5 H 12 D.C 6 H 14 Hydrocarbons CHECK YOUR ANSWER H c c c c c H H H HH H H H H H H

© 2013 Pearson Education, Inc. Hydrocarbons

© 2013 Pearson Education, Inc. Carbon always forms four bonds. Unsaturated Hydrocarbons

© 2013 Pearson Education, Inc. Some of carbon's four bonds, however, may be within multiple bonds. Unsaturated Hydrocarbons

© 2013 Pearson Education, Inc. An unsaturated hydrocarbon is a hydrocarbon that contains one or more multiple bonds. –A special case of an unsaturated hydrocarbon is the benzene ring. Unsaturated Hydrocarbons

© 2013 Pearson Education, Inc. What is the chemical formula for the following structure? A.C 5 H 10 B.C 5 H 12 C.C 6 H 12 D.C 6 H 14 Explain your answer to your neighbor. Unsaturated Hydrocarbons CHECK YOUR NEIGHBOR c c c c c H H H HH H H H H H

© 2013 Pearson Education, Inc. What is the chemical formula for the following structure? A.C 5 H 10 B.C 5 H 12 C.C 6 H 12 D.C 6 H 14 Unsaturated Hydrocarbons CHECK YOUR ANSWER c c c c c H H H HH H H H H H

© 2013 Pearson Education, Inc. A heteroatom is any atom other than hydrogen or carbon in an organic molecule. A functional group is a combination of carbon, hydrogen, and heteroatoms that behave as a single unit. –Organic molecules are classified by the functional groups they contain. Functional Groups

© 2013 Pearson Education, Inc. Functional Groups

© 2013 Pearson Education, Inc. A.B.C.D. Functional Groups CHECK YOUR NEIGHBOR In which of the following structures is carbon bonded five times? Explain your answer to your neighbor.

© 2013 Pearson Education, Inc. In which of the following structures is carbon bonded five times? Explanation: Carbon can never be bonded five times! In none of the structures is carbon indicated to be bonded five times. Sorry for the trick question… A.B.C.D. Functional Groups CHECK YOUR ANSWER

© 2013 Pearson Education, Inc. Alcohols, Phenols, and Ethers Hydroxyl group Alcohols contain the hydroxyl group.

© 2013 Pearson Education, Inc. Alcohols, Phenols, and Ethers Methanol (bp 65°C) Ethanol (bp 78°C) 2-Propanol (bp 97°C)

© 2013 Pearson Education, Inc. Alcohols, Phenols, and Ethers Phenols contain the phenol group. Phenol group

© 2013 Pearson Education, Inc. Alcohols, Phenols, and Ethers Phenols are acidic

© 2013 Pearson Education, Inc. Alcohols, Phenols, and Ethers 4-n-Hexylresorcinol Thymol

© 2013 Pearson Education, Inc. Alcohols, Phenols, and Ethers Ethers contain the ether group, an oxygen atom bonded to two carbon atoms. Ether group

© 2013 Pearson Education, Inc. Alcohols, Phenols, and Ethers Dimethyl ether (bp −25°C) Diethyl ether

© 2013 Pearson Education, Inc. Amines and Alkaloids Amines form alkaline solutions. Amine group

© 2013 Pearson Education, Inc. Alcohols, Phenols, and Ethers Ethyl amine Hydroxide ion

© 2013 Pearson Education, Inc. Alcohols, Phenols, and Ethers Caffeine Phosphoric acid Caffeine salt Water soluble

© 2013 Pearson Education, Inc. Which of the following compounds should have a higher boiling point? A.Structure A B.Structure B C.Both should have the same boiling point. D.There is no way to tell. Explain your answer to your neighbor. Amines and Alkaloids CHECK YOUR NEIGHBOR N H O Structure AStructure B

© 2013 Pearson Education, Inc. Which of the following compounds should have a higher boiling point? A.Structure A B.Structure B C.Both should have the same boiling point. D.There is no way to tell. Explanation: Structure B has a hydrogen attached to a strongly electronegative atom, nitrogen. This makes for a polar N—H bond that participates in hydrogen bonding. Amines and Alkaloids CHECK YOUR ANSWER N H O Structure AStructure B

© 2013 Pearson Education, Inc. Carbonyl Compounds A carbonyl is a carbon atom double bonded to an oxygen atom. Carbonyl

© 2013 Pearson Education, Inc. Carbonyl Compounds Ketone group Aldehyde group

© 2013 Pearson Education, Inc. Carbonyl Compounds AcetoneAcetaldehyde

© 2013 Pearson Education, Inc. Carbonyl Compounds Cinnamonaldehyde Benzaldehyde Vanillin

© 2013 Pearson Education, Inc. Carbonyl Compounds Amide group

© 2013 Pearson Education, Inc. Carbonyl Compounds N,N-Diethyl-m-toluamide DEET

© 2013 Pearson Education, Inc. Carbonyl Compounds Carboxyl group

© 2013 Pearson Education, Inc. Carbonyl Compounds Salicylic acid Acetylsalicylic acid Aspirin

© 2013 Pearson Education, Inc. Carbonyl Compounds Ester group

© 2013 Pearson Education, Inc. Carbonyl Compounds Salicylic acid H 2 SO 4 CH 3 OH Methyl salicylate (wintergreen)

© 2013 Pearson Education, Inc. Carbonyl Compounds Penicillin

© 2013 Pearson Education, Inc. The amino acid lysine is shown below. What functional group must be removed in order to produce the very smelly amine cadaverine, which is 1,5-pentanediamine? A.The hydrogen (shown) must be removed and and replaced with an amino (NH 2 ) group. B.Lysine is 1,5-pentanediamine. Nothing has to be removed. C.The carboxyl group must be removed and replaced with a hydrogen. D.One amino group must be removed and replaced with a hydrogen. Explain your answer to your neighbor. Carbonyl Compounds CHECK YOUR NEIGHBOR

© 2013 Pearson Education, Inc. The amino acid lysine is shown below. What functional group must be removed in order to produce the very smelly amine cadaverine, which is 1,5-pentanediamine? A.The hydrogen (shown) must be removed and and replaced with an amino (NH 2 ) group. B.Lysine is 1,5-pentanediamine. Nothing has to be removed. C.The carboxyl group must be removed and replaced with a hydrogen. D.One amino group must be removed and replaced with a hydrogen. Carbonyl Compounds CHECK YOUR ANSWER

© 2013 Pearson Education, Inc. A polymer is a very long organic molecule made by the joining together of smaller organic molecule units known as monomers. Monomer Polymers

© 2013 Pearson Education, Inc. H CC H H CC H HH HH H CC H HH H CC H HH C H H H C H Polymers An addition polymer is a polymer whose mass is equal to the sum of the masses of the monomer units.

© 2013 Pearson Education, Inc. H CC H H CC H HH HH H CC H HH H CC H HH C H H H C H Ethylene Polyethylene C H H C H H Polymers

© 2013 Pearson Education, Inc. Polypropylene C H CC H H CC HH H H CC H HCH 3 CC HH H C HH H Propylene H C H C H CH 3 Polymers

© 2013 Pearson Education, Inc. Polymers

© 2013 Pearson Education, Inc. A condensation polymer is a polymer formed when the joining of monomer units is accompanied by the loss of a small molecule, such as water. Polymers

© 2013 Pearson Education, Inc. Polymers

© 2013 Pearson Education, Inc. Many of the natural product molecules synthesized by plants are formed by the joining together of isoprene monomers via an addition polymerization. A good example is the flavoring molecule citral, which is made of two isoprene units. Find and circle these units in the structure shown to the right. Isoprene (2-methyl-1,3-butadiene) Citral Polymers

© 2013 Pearson Education, Inc. Many of the natural product molecules synthesized by plants are formed by the joining together of isoprene monomers via an addition polymerization. A good example is the flavoring molecule citral, which is made of two isoprene units. Find and circle these units in the structure shown to the right. Citral Polymers Isoprene (2-methyl-1,3-butadiene)

© 2013 Pearson Education, Inc. Beta-carotene is a natural addition polymer made of eight isoprene units. Find and circle these units in the structure shown below. Beta-carotene Isoprene (2-methyl-1,3-butadiene) Polymers

© 2013 Pearson Education, Inc. Isoprene (2-methyl-1,3-butadiene) Beta-carotene Polymers Beta-carotene is a natural addition polymer made of eight isoprene units. Find and circle these units in the structure shown below.