Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Chapter 10 Introduction to Organic Chemistry: Alkanes 10.1 Organic Compounds 1

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Organic Chemistry An organic compound is a compound made from carbon atoms has one or more C atoms has many H atoms may also contain O, S, N, and halogens usually has carbon written first 2

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Organic Compounds Typical organic compounds have covalent bonds have low melting points have low boiling points are flammable are soluble in nonpolar solvents are not soluble in water Vegetable oil is an organic compound and not soluble in water. 3

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Organic vs. Inorganic Propane, C 3 H 8, is an organic compound used as a fuel. NaCl, salt, is an inorganic compound composed of Na + and Cl  ions. Why is propane organic, but NaCl is not? 4

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Comparing Organic and Inorganic Compounds 5

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Identify each characteristic as most typical of compounds that are inorganic or organic. A. Has a high melting point B. Is not soluble in water C. Has the formula CH 3  CH 2  CH 3 D. Has the formula MgCl 2 E. Burns easily in air F. Has covalent bonds 6

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Identify each characteristic as most typical of compounds that are inorganic or organic. A. Has a high melting pointinorganic B. Is not soluble in waterorganic C. Has the formula CH 3  CH 2  CH 3 organic D. Has the formula MgCl 2 inorganic E. Burns easily in airorganic F. Has covalent bondsorganic 7

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Bonding in Organic Compounds In organic compounds, carbon has 4 valence electrons and hydrogen has 1 carbon achieves an octet by forming four bonds, with each line representing 2 electrons CH 4, methane 8

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Tetrahedral Structure of Carbon CH 4 VSEPR theory predicts that a carbon atom with four single, covalent bonds has a tetrahedral shape. Methane is represented using different models: (a) tetrahedron, (b) ball-and- stick model, (c) space-filling model, (d) expanded structural formula. 9

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Tetrahedral Structure of Carbon C 2 H 6 In ethane, each carbon forms covalent bonds to another carbon and three hydrogen atoms each carbon atom retains its tetrahedral shape Ethane, CH 3 ─CH 3 10

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. In molecules with two or more carbon atoms, each carbon atom with four single bonds has a tetrahedral shape. Representations of ethane: (a) tetrahedral shape of each carbon, (b) ball-and-stick model, (c) space-filling model, (d) expanded structural formula. 11 Tetrahedral Structure of Carbon C 2 H 6

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check In the butane molecule, C 4 H 10, predict the shape around each carbon atom. 12

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution In the butane molecule, C 4 H 10, predict the shape around each carbon atom. Each carbon atom has four single covalent bonds and therefore a tetrahedral shape. 13

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Chapter 10 Introduction to Organic Chemistry: Alkanes 10.2 Alkanes 14

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Alkanes Alkanes are organic molecules containing primarily C–C single bonds commonly used as fuels for heaters and cooktops whose names end in ane named by using the number of carbon atoms connected in a continuous chain 15

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. IUPAC Naming of the First Ten Alkanes 16

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Condensed Structural Formulas In a condensed structural formula, each carbon atom and its attached hydrogen atoms are written as a group a subscript indicates the number of hydrogen atoms bonded to each carbon atom of butane, four carbon atoms are attached in a straight line CH 3  CH 2  CH 2  CH 3 butane 17

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Condensed Structural Formulas Alkanes are written with structural formulas that are expanded to show each bond condensed to show each carbon atom and its attached hydrogen atoms Expanded Condensed Expanded Condensed 18

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Writing Structural Formulas Carbon atoms in a chain maintain tetrahedral shape are connected in a zigzag pattern are drawn as two-dimensional can be written in several conformations 19

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Expanded, Condensed, and Skeletal Structures 20 A hexane molecule can be represented in several ways: a molecular formula a ball-and-stick model an expanded structural formula a condensed structural formula a skeletal formula

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Expanded, Condensed, and Skeletal Structures for C 4 H 10 21

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check 1. Write the expanded structural formula for the following: 2. What is its molecular formula? 3. What is its condensed structural formula? 4. What is its name? 22

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution 1.Write the expanded structural formula for the following: 2.What is its molecular formula? C 5 H 12 3.What is its condensed structural formula? CH 3  CH 2  CH 2  CH 2  CH 3 4.What is its name? pentane 23

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Write the condensed structural formula for A. ethane B. heptane 24

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Write the condensed structural formula for A. ethane CH 3  CH 3 B. heptane CH 3  CH 2  CH 2  CH 2  CH 2  CH 2  CH 3 25

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Sample Problem 10.1 Drawing Expanded and Condensed Structural Formulas for Alkanes In the expanded structural formula, five carbon atoms are connected to each other and to hydrogen atoms using single bonds to give each carbon atom a total of four bonds. In the condensed structural formula, each carbon atom and its attached hydrogen atoms are written as CH3– or –CH2–.The skeletal formula shows the carbon skeleton as a zigzag line where the ends and corners represent C atoms. Study Check 10.1 Draw the condensed structural formula and give the name for the following skeletal formula: Solution Draw the expanded structural formula, condensed structural formula, and skeletal formula for pentane.

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Cycloalkanes are cyclic alkanes have two less hydrogen atoms than the open chain are named by using the prefix cyclo before the name of the alkane chain with the same number of carbon atoms propane, C 3 H 8 cyclopropane, C 3 H 6 27

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Formulas of Cycloalkanes 28

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check 29 Give the IUPAC name for each of the following compounds: A. B.

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution 30 Give the IUPAC name for each of the following compounds: A. An alkane with eight continuous carbon atoms is octane. B. A cyclic molecule with five carbons is cyclopentane.

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Name the following alkanes: A. CH 3  CH 2  CH 2  CH 3 B. C. CH 3  CH 2  CH 2  CH 2  CH 2  CH 2  CH 2  CH 3 D. 31

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Name the following alkanes: A. CH 3  CH 2  CH 2  CH 3 butane B.cyclopropane C. CH 3  CH 2  CH 2  CH 2  CH 2  CH 2  CH 2  CH 3 octane D. cyclohexane 32

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Sample Problem 10.2 Naming Alkanes a. A chain with eight carbon atoms is octane. b. The ring of six carbon atoms is named cyclohexane. Study Check 10.2 What is the IUPAC name of the following compound? Solution Give the IUPAC name for each of the following: a. b.

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Chapter 10 Introduction to Organic Chemistry: Alkanes 10.3 Alkanes with Substituents 34

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Isomers of Butane Isomers have the same molecular formula with different atom arrangements of butane (C 4 H 10 ) are a straight chain and a branched chain The isomers of butane have the same number and type of atoms, but the atoms are bonded in a different order. 35

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Sample Problem 10.3 Isomers a. Although the carbon chain has different angles due to rotation, these condensed structural formulas represent the same molecule. The two formulas represent thesame molecule because each has four C atoms in a continuous chain. b. The molecular formula of both these condensed structural formulas is C6H14. However, they represent isomers because the C atoms are bonded in a different order; they have different arrangements. In one, there is a –CH 3 group attached to a five-carbon chain, and in the other there are two –CH 3 groups attached to a four-carbon chain. Study Check 10.3 Why is the following condensed structural formula an isomer of the molecules in Sample Problem 10.3, part b? Solution Identify each pair of condensed structural formulas as isomers or the same molecule. a. b.

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Substituents and Alkyl Groups Substituents are atoms or groups of atoms attached to the carbon chain and include alkyl and halo groups. Alkyl groups are carbon branches attached to carbon chains named with a yl ending Halo substituents are halogens attached to the carbon chain named as fluoro, chloro, bromo, or iodo 37

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Substituents and Alkyl Groups 38

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Guide to Naming Alkanes with Substituents 39

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Write IUPAC Names for Alkanes with Substituents Give the IUPAC name for the following compound: Step 1 Write the alkane name of the longest chain of carbon atoms. The longest chain has five carbons, pentane. 40

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Write IUPAC Names for Alkanes with Substituents Step 2 Number the carbon atoms starting from the end nearer a substituent. Step 3 Give the location and name of each substituent (in alphabetical order) as a prefix to the name of the main chain. 2-chloro-3-methylpentane 41

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Give the IUPAC name for the following compound: 42

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Give the IUPAC name for the following compound: Step 1 Write the alkane name of the longest chain of carbon atoms. The longest chain has four carbons, butane. 43

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Step 2 Number the carbon atoms starting from the end nearer a substituent. Step 3 Give the location and name of each substituent (in alphabetical order) as a prefix to the name of the main chain. 1,2-dibromo-3-methylbutane 44

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Sample Problem 10.4 Writing IUPAC Names for Alkanes with Substituents Step 1Write the alkane name of the longest chain of carbon atoms. In this alkane, the longest chain has six carbon atoms, which is hexane. Step 2Number the carbon atoms starting from the end nearer a substituent. The numbering of the carbon chain begins at carbon 1 at the end of the carbon chain closer to the methyl group (CH3–)and continues in the same direction. Solution Give the IUPAC name for the following alkane:

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Step 3Give the location and name of each substituent (alphabetical order) as a prefix to the name of the main chain. The substituents, which are bromo and methyl groups, are listed in alphabetical order. A hyphen is placed between the number on the carbon chain and the substituent name. When there are two or more of the same substituent, a prefix (di, tri, tetra) is used in front of the name. Then commas are used to separate the numbers for the locations of the substituents. Solution Continued Sample Problem 10.4 Writing IUPAC Names for Alkanes with Substituents Study Check 10.4 Give the IUPAC name for the following compound:

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming Cycloalkanes with Substituents Give the IUPAC name for the following cycloalkane. Step 1 Write the alkane name of the longest chain of carbon atoms. The longest chain is a six-member ring, cyclohexane. 47

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Step 2 Number the carbon atoms starting from the end nearer a substituent. Step 3 Give the location and name of each substituent (in alphabetical order) as a prefix to the name of the main chain. For cycloalkanes with just one substituent, there is no need to give the location of the substituent: ethylcyclohexane 48

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Sample Problem 10.5 Naming Haloalkanes Freon-11, trichlorofluoromethane; Freon-12, dichlorodifluoromethane Study Check 10.5 A haloalkane used as a fumigant has two carbon atoms with one bromine atom attached to each carbon. What is its IUPAC name? Solution Freon-11 and Freon-12 are compounds, known as chlorofluorocarbons (CFCs), previously used as refrigerants and aerosol propellants. What are their IUPAC names?

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Drawing Formulas for Alkanes 50 Draw the structure for 1-chloro-1,2-dimethylheptane heptane – 7-carbon chain methyl group on carbon 1 and 2 chlorine on carbon 1

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Guide to Drawing Formulas for Alkanes 51

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Draw the condensed structural formula for 3-bromo-1-chlorobutane. 52

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Draw the condensed structural formula for 3-bromo-1-chlorobutane. Step 1Draw the main chain of carbon atoms. The longest chain in butane has four carbon atoms.C  C  C  C Step 2Number chain and place the substituents on the carbons indicated by the numbers bromo:  Br goes on carbon 3. C  C  C  C Cl Br 1-chloro:  Cl goes on carbon 1. 53

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Draw the condensed structural formula for 3-bromo-1-chlorobutane. Step 3 Add hydrogen to complete four bonds to each carbon. CH 2  CH 2  CH  CH 3   Cl Br 3-bromo-1-chlorobutane 54

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Name each of the following cycloalkanes. A. B. C. 55

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Name each of the following cycloalkanes. A. methylcyclopropane B. ethylcyclobutane C. chlorocyclopentane 56

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Sample Problem 10.6 Drawing Condensed Structures from IUPAC Names Solution Draw the condensed structural formula and skeletal formula for 2,3-dimethylbutane. We can use the following guide to draw the condensed structural formula: Step 1Draw the main chain of carbon atoms. For butane, we draw a chain of four carbon atoms. C–C–C–CC–C–C–C Step 2Number the chain and place the substituents on the carbons indicated by the numbers. The first part of the name indicates two methyl groups (CH 3 –),one on carbon 2 and one on carbon 3. Step 3Add the correct number of hydrogen atoms to give four bonds to each C atom. Study Check 10.6 What is the condensed structural formula and skeletal formula for 2-bromo-4-methylpentane?

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Chapter 10 Introduction to Organic Chemistry: Alkanes 10.4 Properties of Alkanes 58

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Some Uses of Alkanes Alkanes with one to four carbons are gases at room temperature and are widely used as heating fuels. methane, ethane, propane, butane Butane has four carbons: Alkanes with five to eight carbons are highly volatile liquids at room temperature, making them useful in fuels such as gasoline. pentane, hexane, heptane, octane Octane has eight carbons: 59

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Some Uses of Alkanes Alkanes with 9−17 carbons are liquids with higher boiling points and are found in motor oils, mineral oil, kerosene, diesel, and jet fuels. Decane has 10 carbons: 60

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Some Uses of Alkanes Alkanes with 18 or more carbon atoms have high molar masses are waxy solids at room temperature are used in waxy coatings of fruits and vegetables 61

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solubility and Density of Alkanes Alkanes are nonpolar insoluble in water less dense than water flammable in air The crude oil in oil spills floats on top of the water, forming a thin layer on the surface because it is less dense than water. 62

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Combustion of Alkanes Alkanes have strong C  C bonds react with oxygen gas to make carbon dioxide and water in combustion reactions release energy when C  C bonds are broken in combustion reactions CH 4 (g) + 2O 2 (g)  CO 2 (g) + 2H 2 O(g) + energy 63

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Alkane Mixtures in Crude Oil An oil refinery turns crude oil into usable fuel, producing natural gas, gasoline, kerosene, lubricant oils, and asphalt. 64

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Alkane Mixtures in Crude Oil 65

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Propane is a fuel often used in barbeques. Write a balanced equation for the complete combustion of propane. 66

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Unbalanced equation: C 3 H 8 + O 2 CO 2 + H 2 O Balance C: C 3 H 8 + O 2 3CO 2 + H 2 O Balance H: C 3 H 8 + O 2 3CO 2 + 4H 2 O Balance O: C 3 H 8 + 5O 2 3CO 2 + 4H 2 O (balanced) 67

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Chapter 10 Introduction to Organic Chemistry: Alkanes 10.5 Functional Groups 68

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Elements in Organic Compounds In organic molecules, carbon atoms bond with four bonds mostly with H and other C atoms sometimes to O, N, S sometimes to halogens F, Cl, and Br 69

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Elements in Organic Compounds 70

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Functional Groups Functional groups are a characteristic feature of organic molecules that behave in a predictable way composed of an atom or group of atoms groups that replace a hydrogen atom in the corresponding alkane a way to classify families of organic compounds 71

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Alkenes, Alkynes, and Aromatic Compounds Alkenes contain a double bond between adjacent carbon atoms. Alkynes contain a triple bond. Aromatic compounds contain a ring of six carbon atoms called benzene. 72

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Comparing Alkenes, Alkynes, and Aromatic Compounds 73

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check 74 Identify the following compounds as an alkene, alkyne, or aromatic compound. A. B. C.

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution 75 Identify the following compounds as an alkene, alkyne or aromatic compound. A.aromatic B.alkene C.alkyne

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Alcohols, Thiols, and Ethers An alcohol contains the hydroxyl (−OH) functional group. A thiol contains the thiol (−SH) functional group. An ether contains an oxygen atom bonded to two carbon atoms (C  O  C) functional group. 76

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Aldehydes and Ketones An aldehyde contains a carbonyl group (C=O), which is a carbon atom with a double bond to an oxygen atom. The carbonyl carbon is attached to a hydrogen. In a ketone, the carbon of the carbonyl group (C=O) is attached to two carbon atoms. 77

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Carboxylic Acids and Esters Carboxylic acids contain the carboxyl group, which is a carbonyl group attached to a hydroxyl group.  COOH An ester contains the carboxyl group between carbon atoms.  COOCH 3 78

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Amines have a functional group that contains a nitrogen atom are derivatives of ammonia, NH 3, in which one, two, or three hydrogen atoms are replaced with carbons 79

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Amides have an amine group instead of an  OH group on the carbonyl carbon are an important biological functional group, the simplest amide being urea 80

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Classification of Organic Compounds 81

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Classify each of the following as an alcohol, ether, aldehyde, ketone, carboxylic acid, ester, amine, or amide. A. B. C. D. E. 82

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Classify each of the following as an alcohol, ether, aldehyde, ketone, carboxylic acid, ester, amine, or amide. A. B. C. D. E. 83 alcohol ether amine carboxylic acid ester

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Concept Map – Organic Compounds 84

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Sample Problem 10.7 Classifying Organic Compounds a. alcohol b. amine c. ketone d. carboxylic acid Study Check 10.7 Classify the following organic compound according to its functional group: Solution Classify the following organic compounds according to their functional groups: a. CH 3 –CH 2 –CH 2 –CH 2 –OH b. CH 3 –CH 2 –NH–CH 3 c. d.