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ORGANIC CHEMISTRY Any molecule that contains the element CARBON SUBSTITUTED HYDROCARBONS Organic Chemistry Hydrocarbons ONLY Carbon and Hydrogen Alkene Alkane Alkyne Ring (Benzene) Substituded Substituded Hydrocarbons Hydrocarbons + Halogens + Oxygen Substituded Hydrocarbons + Nitrogen Amine Amide Alcohol aldehyde organic acid ketone ester ether Substituted Hydrocarbons 23.1 Introduction to Functional Groups Organic compounds > can be classified according to their functional groups. A functional group is a specific arrangement of atoms in an organic compound that identify it as part of a specific family. Note that the double and triple bonds of alkenes and alkynes are considered the functional groups. 5 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. Identify the Functional Group 23.1 Introduction to Functional Groups > Halocarbons What is the general formula of a halocarbon? • A halocarbon is an organic compound that contains at least one covalently bonded fluorine, chlorine, bromine, or iodine atom. Chloroethene 7 Chloromethane Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. 23.1 Introduction to Functional Groups > Alcohols What do mouthwash, perfume, and hairspray have in common? They all contain an alcohol of some type. An alcohol is an organic compound with an —OH group. Ethanol 8 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. 23.1 Introduction to Functional Groups 9 > Interpret Data Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. Compounds with Oxygen Atoms Alcohols • contain a hydroxyl group (-OH) Phenols • contain a benzene ring with a hydroxyl group. 10 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Alcohols are named • with an IUPAC name that replaces the e in alkane name with ol CH4 methane CH3─OH methanol CH3─CH3 ethane CH3─CH2─OH ethanol 11 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Naming Alcohols 12 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Name the following Alcohol CH3 OH │ │ CH3─CH─CH2─CH2─CH─CH3 STEP 1 Name the longest carbon chain with the OH group. A six-carbon chain attached to an OH is hexanol 13 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Naming an Alcohol (continued) STEP 2 Number the chain starting at the end closer to the OH group. CH3 OH │ │ CH3─CH─CH2─CH2─CH─CH3 6 5 4 3 2 1 STEP 3 Give the location and name of each substituent relative to the OH group. 5-methyl-2-hexanol 14 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Name the CH3 following: │ CH3─CH2─CH ─CH2─OH 4 3 2 1 STEP 1 Name the longest carbon chain with the OH group. A four-carbon chain attached to an OH is butanol. STEP 2 Number the chain starting at the end closer to the OH group. STEP 3 Give the location and name of each substituent relative to the OH group. 2-methyl-1-butanol 15 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Give the IUPAC name for the following: OH CH3 | | CH3—CH—CH—CH2—CH3 1 2 3 4 5 STEP 1 Name the longest carbon chain with the OH group. A five-carbon chain attached to an OH is pentanol. STEP 2 Number the chain starting at the end closer to the OH group. STEP 3 Give the location and name of each substituent relative to the OH group. 16 Basic Chemistry 3-methyl-2-pentanol Copyright © 2011 Pearson Education, Inc. 23.3 Carbonyl Compounds > Carboxylic Acids The general formula of a carboxylic acid is RCOOH. 17 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. 23.3 Carbonyl Compounds > Carboxylic Acids In the IUPAC system, carboxylic acids are named by replacing the -e ending of the parent structure with the ending -oic acid. • The carboxylic acid CH3COOH is named ethanoic acid. 18 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. 23.3 Carbonyl Compounds > Interpret Data Some Saturated Aliphatic Carboxylic Acids Molecular formula 19 Carbon IUPAC name atoms Common name Melting point (°C) HCOOH 1 Methanoic acid Formic acid 8 CH3COOH 2 Ethanoic acid Acetic acid 17 CH3CH2COOH 3 Propanoic acid Propionic acid CH3(CH2)2COOH 4 Butanoic acid Butyric acid –6 CH3(CH2)4COOH 6 Hexanoic acid Caproic acid –3 CH3(CH2)6COOH 8 Octanoic acid Caprylic acid 16 CH3(CH2)8COOH 10 Decanoic acid Capric acid 31 CH3(CH2)10COOH 12 Dodecanoic acid Lauric acid 44 CH3(CH2)12COOH 14 Tetradecanoic acid Myristic acid 58 CH3(CH2)14COOH 16 Hexadecanoic acid Palmitic acid 63 CH3(CH2)16COOH 18 Octadecanoic acid 70 Stearic acid –22 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. 23.3 Carbonyl Compounds > Carboxylic Acids Lemons and limes contain citric acid, a carboxylic acid that gives citrus fruits their sour flavor. 20 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. Carboxylic acids are named • in the IUPAC system by replacing the e in the alkane name of the longest carbon chain with oic acid H─COOH methanoic acid formic acid CH3─COOH ethanoic acid acetic acid CH3─CH2─COOH propanoic acid CH3─CH2─CH2─COOH 21 Basic Chemistry butanoic acid Copyright © 2011 Pearson Education, Inc. Naming Carboxylic Acids 22 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Give the IUPAC name of the following Carboxylic Acid CH3 | CH3—CH—CH2—COOH STEP 1 Identify the carbon chain containing the carboxyl group and replace the e in the alkane name with oic acid. butanoic acid 23 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Example of Naming a Carboxylic Acid (continued) STEP 2 Give the location and name of each substituent on the main chain by counting the carboxyl group as carbon 1. CH3 | CH3—CH—CH2—COOH 4 3 2 1 3-methylbutanoic acid 24 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Give the IUPAC name for the CH CH following: 3 3 | | CH3─CH─CH2─CH─COOH 5 4 3 2 1 STEP 1 Identify the carbon chain containing the carboxyl group and replace the e with oic acid. pentanoic acid STEP 2 Give the location and name of each substituent on the main chain by counting the carboxyl group as carbon 1. 2,4-dimethylpentanoic acid 25 Basic Chemistry Copyright © 2011 Pearson Education, Inc. 23.3 Carbonyl Compounds > Aldehydes and Ketones Aldehydes and Ketones What structural characteristic do an aldehyde and a ketone share? • A carbonyl group: it is a functional group with the general structure C O. 26 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. 23.3 Carbonyl Compounds > Interpret Data Some Common Aldehydes IUPAC name (common name) Structural formula Ball-and-stick model Methanal (formaldehyde) Ethanal (acetaldehyde) Benzaldehyde (benzaldehyde) 27 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. 23.3 Carbonyl Compounds > Interpret Data Some Common Ketones IUPAC name (common name) Structural formula Ball-and-stick model Propanone (acetone) Diphenylmethanone (benzophenone) 28 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. 23.3 Carbonyl Compounds > 29 29 Naming Aldehydes 23.3 Carbonyl Compounds > Give the IUPAC name for the following: Aldehyde Cl O │ ║ CH3─CH2─CH─CH2─C─H STEP 1 Name the longest carbon chain containing the carbonyl group by replacing the e in the alkane name with al. pentanal 30 30 Aldehyde (continued) 23.3 Carbonyl Compounds > STEP 2 Name and number substituents by counting the carbonyl group as carbon 1. Cl O │ ║ CH3─CH2─CH─CH2─C─H 5 4 3 2 1 3-chloropentanal 31 31 23.3 Carbonyl Compounds > Draw the condensed structural formula for 2,3-dichloropropanal. STEP 1 Draw the main chain of carbon atoms. Propanal has three carbon atoms with an aldehyde group. O ║ C─C─C─H 3 2 1 STEP 2 Number the chain and place the substituents on carbons indicated by the numbers. 32 32 23.3 Carbonyl Compounds > Solution (continued) Cl Cl O │ │ ║ C─C─C─H 3 2 1 STEP 3 Add the correct number of hydrogen atoms. Cl Cl O │ │ ║ CH2─CH─C─H 2,3-dichloropropanal 33 33 23.3 Carbonyl Compounds > Naming Ketones In the name for a ketone, the • IUPAC name replaces the e in the alkane name by one • common name identifies the alkyl groups attached to the carbonyl group in alphabetical order and adds the word ketone 34 34 23.3 Carbonyl Compounds > 35 35 Naming Ketones 23.3 Carbonyl Compounds > Give the IUPAC name for the following Ketone O ║ Cl─CH2─CH2─C─CH2─Cl STEP 1 Name the longest carbon chain containing the carbonyl group by replacing the e in the alkane name with one. butanone 36 36 Naming a Ketone (continued) 23.3 Carbonyl Compounds > STEP 2 Number the carbon chain starting from the end nearer the carbonyl group and indicate its location. O ║ 2-butanone Cl─CH2─CH2─C─CH2─Cl 4 3 2 1 STEP 3 Name and number any substituents on the carbon chain. 1,4-dichloro-2-butanone 37 37 23.3 Carbonyl Compounds > name for the following: CH3 O │ ║ CH3─CH2─CH─C─CH2─CH3 STEP 1 Name the longest carbon chain containing the carbonyl group by replacing the e in the alkane name with one. hexanone 38 38 23.3 Carbonyl Compounds > Solution STEP 2 Number the carbon chain starting from the end nearer the carbonyl group and indicate its location. CH3 O │ ║ CH3─CH2─CH─C─CH2─CH3 6 5 4 3 2 1 3-hexanone STEP 3 Name and number any substituents on the carbon chain. CH3 O │ ║ CH3─CH2─CH─C─CH2─CH3 6 5 4 39 39 3 2 1 4-methyl-3-hexanone 23.1 Introduction to Functional Groups > Ethers What is the general formula of an ether? • An ether is an organic compound in which oxygen is bonded to two carbon groups. 40 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. 23.1 Introduction to Functional Groups > Ethers Diethyl ether was the first reliable general anesthetic. • However, because diethyl ether is highly flammable and often causes nausea, it was eventually replaced by other anesthetics. 41 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. Ethers • contains an ─O─ between two carbon atoms • has a common name of the two alkyl names followed by ether 42 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Write the condensed structural formula of diethyl ether. This ether contains an ─O─ attached to two ethyl groups (CH3─CH2─ ). CH3─CH2─O─CH2─CH3 43 Basic Chemistry Copyright © 2011 Pearson Education, Inc. 23.3 Carbonyl Compounds > Esters Esters are probably the most pleasant and delicious organic compounds one can study. • Many esters have pleasant, fruity odors. • Esters give blueberries, pineapples, apples, pears, bananas, and many other fruits their characteristic aromas. • They also give many perfumes their fragrances. 44 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. 23.3 Carbonyl Compounds > Esters The general formula of an ester is RCOOR. 45 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. Esterification • is the reaction between a carboxylic acid and an alcohol • uses an acid catalyst and heat O ║ H+, heat CH3 — C—OH + HO—CH2—CH3 O ║ CH3 — C—O—CH2—CH3 + H2O 46 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Write the equation for the reaction of propanoic acid and methyl alcohol when heated in the presence of an acid catalyst. O ║ H+, heat CH3—CH2—C—OH + HO—CH3 O ║ CH3—CH2—C—O—CH3 + H2O 47 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Esters In an ester, the H in the carboxyl group is replaced with an alkyl group. O ║ CH3—C—O—CH3 ester group 48 Basic Chemistry The ester methyl ethanoate (methyl acetate) is made from methyl alcohol and ethanoic acid (acetic Copyright acid). © 2011 Pearson Education, Inc. The name of an ester includes • name of the alkyl group from the alcohol • the name of the carbon chain from the acid with the ic acid ending replaced by ate 49 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Naming Esters 50 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Example of Naming an Ester Give the IUPAC and common names of the following compound, which is responsible for the flavor and odor of pears: O ║ CH3—C—O—CH2—CH2—CH3 STEP 1 Write the name of the carbon chain from the alcohol as an alkyl group. The alkyl group with three carbon atoms is propyl. 51 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Example of Naming an Ester (continued) STEP 2 Change the ic acid of the acid name to ate. In the IUPAC name, ethanoic acid is named ethanoate. O ║ propyl CH3—C—O—CH2—CH2—CH3 ethanoate propyl ethanoate (IUPAC) propyl acetate (common) 52 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Give the IUPAC for the following O ║ CH3—CH2—CH2—C—O—CH2—CH3 STEP 1 Write the name of the carbon chain from the alcohol as an alkyl group. ethyl STEP 2 Change the ic acid of the acid name to ate. O butanoate ║ ethyl CH3—CH2—CH2—C—O—CH2—CH3 53 ethyl butanoate (IUPAC) Basic Chemistry Copyright © 2011 Pearson Education, Inc. Draw the condensed structural formula of ethyl propionoate. O propionate ║ ethyl CH3—CH2 —C—O—CH2—CH3 54 Basic Chemistry Copyright © 2011 Pearson Education, Inc. 23.1 Introduction to Functional Groups > Amines Ethanamine What is the general formula of an amine? • An amine is an organic compound in which nitrogen is bonded to a carbon group. 55 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. Amines • are derivatives of ammonia, NH3 • contain N attached to one or more alkyl or aromatic groups 56 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Naming Simple Amines Simple amines have common names that list the alkyl groups attach to the N atom followed by amine. 57 Basic Chemistry Copyright © 2011 Pearson Education, Inc. 23.1 Introduction to Functional Groups > Amines The -e ending of the parent hydrocarbon is changed to -amine. – Ethanamine is used to make plastics, pharmaceuticals, and pesticides. – Benzenamine is used to make furniture foam and some of the dyes that give clothes their colors. Benzenamine Ethanamine 58 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved. Learning Check Give the common name for each of the following: A. CH3—NH—CH2—CH3 ethylmethylamine B. CH3 | CH3—CH2—N—CH2—CH3 diethylmethylamine 59 Basic Chemistry Copyright © 2011 Pearson Education, Inc. Draw the condensed structural formulas for methylpropylamine CH3–CH2–CH2–NH–CH3 60 Basic Chemistry Copyright © 2011 Pearson Education, Inc. 23.1 Introduction to Functional Groups > Identify Family and Functional Group Amine aldehyde Alkene Ketone Acid Alkane 61 alcohol acid halogen alcohol halogen acid ester alcohol Chapter 17 – Organic Chemistry 4. The IUPAC name for isopropyl alcohol is: A. B. C. D. 1–propanol 2–phenol 2–propanol 2–propanol 1,2,3–propanetriol Chapter 17 – Organic Chemistry 5. The correct name of CH3-O-CH2CH3 is: A. B. C. D. diethyl ether ethyl ether methyl ethyl methyl ethylether ether ethyl methyl oxide Concept Map 65 Basic Chemistry Copyright © 2011 Pearson Education, Inc.