Chapter 10 Introduction to Organic Chemistry: Alkanes. Organic Chemistry Organic Compounds. Organic vs. Inorganic.

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1 Chapter 10 Introduction to Organic Chemistry: Alkanes 10.1 Organic Compounds 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. 1 2 Organic Compounds Organic vs. Inorganic 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. oil (organic) and water (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? 3 4 Comparing Organic and Inorganic Compounds Identify each characteristic as most typical of compounds that are 1) inorganic or 2) organic. A. has a high melting point. B. is not soluble in water. C. has a formula CH 3 CH 2 CH 3. D. has a formula MgCl 2. E. burns easily in air. F. has covalent bonds. 5 6

2 Solution Identify each characteristic as most typical of compounds that are 1) inorganic or 2) organic. 1 A. has a high melting point. 2 B. is not soluble in water. 2 C. has a formula CH 3 CH 2 CH 3. 1 D. has a formula MgCl 2. 2 E. burns easily in air. 2 F. has covalent bonds. Writing Formulas for Alkanes In organic compounds, carbon has 4 valence electrons and hydrogen has 1. C H carbon achieves an octet by forming four bonds. H H H : C : H H C H H H CH 4, methane 7 8 Tetrahedral Structure of Carbon Organic Molecules VSEPR theory predicts that a carbon atom with four single, covalent bonds has a tetrahedral shape. In organic molecules, valence electrons are shared. covalent bonds form between carbon atoms. H H H H H : C : C : H H C C H H H H H Ethane, CH 3 CH Tetrahedral Structure of Carbon In molecules with two or more carbon atoms, each carbon atom with four single bonds has a tetrahedral shape. Chapter 10 Introduction to Organic Chemistry: Alkanes 10.2 Alkanes 11 12

3 Structural Formulas Expanded and Condensed Structures 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 H Condensed H C H CH 4, methane H Structural Formulas Condensed formulas are written for expanded structural formula by showing each carbon and the attached hydrogen atoms. Expanded Condensed H H H H H C C C C H CH 3 CH 2 CH 2 CH 3 H H H H Names of Alkanes The names of alkanes are determined by the IUPAC (International Union of Pure and Applied Chemistry) system. end in ane. with 1-4 carbons in a chain use prefixes as follows: Name # Carbons Condensed Structural Formula Methane 1 CH 4 Ethane 2 CH 3 CH 3 Propane 3 CH 3 CH 2 CH 3 Butane 4 CH 3 CH 2 CH 2 CH Names of Alkanes Alkanes with 5-10 carbon atoms in a chain use Greek prefixes. Name # Carbons Structural Formula Pentane 5 CH 3 CH 2 CH 2 CH 2 CH 3 Hexane 6 CH 3 CH 2 CH 2 CH 2 CH 2 CH 3 Heptane 7 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 Octane 8 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 Nonane 9 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 Decane 10 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 A. Write the condensed formula for: H H H H H H C C C C C H H H H H H B. What is its molecular formula? C. What is its name? 17 18

4 Solution Writing Structural Formulas A. CH 3 CH 2 CH 2 CH 2 CH 3 B. C 5 H 12 C. pentane Carbon atoms in a chain maintain tetrahedral shape. are connected in a zigzag pattern. are drawn as 2-dimensional. can be written in several conformations Some Structures for Butane Hexane Has Six Carbon Atoms Hexane is an alkane with six carbon atoms in a continuous chain. has a zigzag look because each carbon atom is at the center of a tetrahedron. is represented by a ball-and-stick model as shown below Solution Write the condensed structural formula for A. ethane. Write the condensed structural formula for A. ethane CH 3 CH 3 B. heptane. B. heptane CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH

5 Cycloalkanes Cycloalkanes Cycloalkanes The structural formulas of cycloalkanes are usually represented by geometric figures. are cyclic alkanes. have two hydrogen atoms fewer 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 More Cycloalkanes Name the following. 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 Solution Name the following: A. CH 3 CH 2 CH 2 CH 3 butane Chapter 10 Introduction to Organic Chemistry: Alkanes 10.3 Alkanes with Substituents B. cyclopropane C. CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 octane D. cyclohexane 29 30

6 Isomers of Butane Isomers have the same molecular formula. have different atom arrangements. of butane (C 4 H 10 ) are a straight chain and a branched chain. Alkyl groups Alkyl groups are alkanes that are missing one H. substituents attached to carbon chains. named with a yl ending. CH 3 methyl CH 3 CH 2 ethyl Naming Substituents Guide to Naming Alkanes In the IUPAC system, a carbon branch is named as an alkyl group. halogen atoms are named as halo Alkanes with Substituents Naming Alkanes CH 3 Give the name of CH 3 CH 3 CH 3 CH CH 3 methylpropane methyl groups CH 3 CH 3 CH 3 CH CH 2 CH CH 3 2,4-dimethylpentane STEP 1: CH 3 CH CH CH 3 Name the longest continuous chain. CH 3 CH 3 CH 3 CH CH CH 3 butane 35 36

7 Naming Alkanes Give the name of CH 3 CH 3 CH 3 CH CH CH 3 STEP 2: Number chain. CH 3 CH 3 CH 3 CH CH CH STEP 3: Locate substituents and name. 2,3-dimethylbutane Write the name of Cl CH 3 CH 3 CH 2 CH CH CH Solution STEP 1: Longest chain is pentane. Give the IUPAC name for each of the following: STEP 2: STEP 3: Number chain from end nearest substituent. Cl CH 3 CH 3 CH 2 CH CH CH Locate substituents and name alphabetically. 3-chloro-2-methylpentane A. CH 3 CH 3 CH 3 CH CH 2 CH CH 3 B. Cl CH 3 CH 3 CH 2 CH CH 2 C CH 2 CH 3 Cl Solution Guide to Drawing Alkane Formulas A. CH 3 CH 3 CH 3 CH CH 2 CH CH ,4-dimethylpentane B. Cl CH 3 more substituents on C3 CH 3 CH 2 CH CH 2 C CH 2 CH 3 Cl ,5-dichloro-3-methylheptane 41 42

8 Draw the condensed structural formula for 3-bromo-1-chlorobutane. Solution 3-bromo-1-chlorobutane STEP 1: Longest chain has 4 carbon atoms. C C C C STEP 2: Number chain and add substituents. Br C C C C Cl STEP 3: Add hydrogen to complete 4 bonds to each C. Br CH 3 CH CH 2 CH 2 Cl Naming Cycloalkanes with Substituents The name of a substituent is placed in front of the cycloalkane name. Name each of the following. 1. CH 3 methylcyclobutane CH 3 chlorocyclopentane Cl 2. CH 2 CH Solution Name each of the following. 1. methylcyclopropane Chapter 10 Introduction to Organic Chemistry: Alkanes 10.4 Properties of Alkanes 2. ethylcyclohexane 47 48

9 Some Properties of Alkanes Some Properties of Alkanes Alkanes are nonpolar. insoluble in water. less dense than water. flammable in air. Alkanes with 1-4 carbon atoms are methane, ethane, propane, and butane. gases at room temperature. used as heating fuels Some Properties of Alkanes Some Properties of Alkanes Alkanes with 5-8 carbon atoms are liquids at room temperature. pentane, hexane, heptane, and octane. very volatile. used to make gasoline. Alkanes with 18 or more carbon atoms have high molar masses. are waxy solids at room temperature. used in waxy coatings of fruits and vegetables. Alkanes with 9-17 carbon atoms are liquids at room temperature have higher boiling points. are found in kerosene, diesel, and jet fuels Combustion In combustion reactions, alkanes react with oxygen. CO 2, H 2 O, and energy are produced. Alkane + O 2 CO 2 + H 2 O + heat Write a balanced equation for the complete combustion of propane

10 Solution Unbalanced equation C 3 H 8 + O 2 Balance C C 3 H 8 + O 2 Balance H C 3 H 8 + O 2 Balance O C 3 H 8 + 5O 2 CO 2 + H 2 O 3CO 2 + H 2 O 3CO 2 + 4H 2 O 3CO 2 + 4H 2 O (Balanced) Chapter 10 Introduction to Organic Chemistry: Alkanes 10.5 Functional Groups Elements in Organic Compounds Functional Groups 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. 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 Alkenes, Alkynes, and Aromatic Compounds Comparing 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

11 Alcohols and Ethers Aldehydes and Ketones 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. An aldehyde contains a carbonyl group (C=O), which is a carbon atom with a double bond to an oxygen atom. The carbonyl is attached to a hydrogen. In a ketone, the carbon of the carbonyl group (C=O) is attached to two carbon atoms. Copyright 2009 by Pearson Education, Inc, Carboxylic Acids and Esters Amines and Amides Carboxylic acids contain the carboxyl group, which is a carbonyl group attached to a hydroxyl group. O C OH An ester contains the carboxyl group between carbon atoms. In amines, the functional group is a nitrogen atom. N In amides, the hydroxyl group of a carboxylic acid is replaced by a nitrogen group. Amines An amide Summary of Functional Groups Classify each of the following as: alcohol, ether, aldehyde, ketone, carboxylic acid, ester, amine, or amide. 1) CH 3 CH 2 CH 2 OH 2) CH 3 O CH 2 CH 3 3) CH 3 CH 2 NH 2 O O 4) CH 3 C OH 5) CH 3 C O CH

12 Solution 1) CH 3 CH 2 CH 2 OH alcohol 2) CH 3 O CH 2 CH 3 ether 3) CH 3 CH 2 NH 2 amine O O 4) CH 3 C OH 5) CH 3 C O CH 3 carboxylic acid ester 67

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