Organic Chemistry Nomenclature Workbook By: Rebekah ODonnell Organic Chemistry Nomenclature Workbook By: Rebekah ODonnell Online: < http://cnx.org/content/col29252/1.3/ > This selection and arrangement of content as a collection is copyrighted by Rebekah ODonnell. It is licensed under the Creative Commons Attribution License 4.0 (http://creativecommons.org/licenses/by/4.0/). Collection structure revised: May 13, 2019 PDF generated: May 18, 2019 For copyright and attribution information for the modules contained in this collection, see p. 93. Table of Contents 1 Unbranched Alkanes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1 2 Constitutional Isomers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3 3 Alkyl Substituents . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 7 4 Alkenes and Alkynes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 17 5 Halogens . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 27 6 Benzene and Conjugation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 33 7 Alcohols . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 41 8 Ethers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 49 9 Aldehydes and Ketones . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 53 10 Carboxylic acids and Esters . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 67 11 Amines and Amides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 83 Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 92 Attributions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 93 iv Available for free at Connexions <http://cnx.org/content/col29252/1.3> Chapter 1 Unbranched Alkanes 1 An alkane is a type of hydrocarbon (a compound consisting of only carbon and hydrogen atoms). When the carbon-carbon backbone consists only of single bonds, the hydrocarbon contains as many hydrogen atoms saturated. Alkanes are saturated hydrocarbons. Unbranched alkanes have all their carbon atoms in a single chain. as possible, and is therefore Hexane Figure 1.1: Hexane is an unbranched, saturated alkane containing six carbon atoms. Below is a table of the names of unbranched, saturated alkanes containing up to ten carbons, with their condensed structural formulas, molecular formulas, and boiling points. 1 This content is available online at <http://cnx.org/content/m76439/1.4/>. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 1 2 CHAPTER 1. UNBRANCHED ALKANES Alkane Condensed Structural Formula Molecular Formula Boiling Point (degrees C) Methane CH4 CH4 -161 Ethane CH3 CH3 C2 H6 -89 Propane CH3 CH2 CH3 C3 H8 -42 Butane CH3 CH2 CH2 CH3 -0.5 Pentane CH3 (CH2 )3 CH3 36 Hexane CH3 (CH2 )4 CH3 69 Heptane 98 Octane 126 Nonane 151 Decane 174 Table 1.1: Table of names, condensed structural formulas, molecular formulas, and boiling points of unbranched saturated alkanes containing up to ten carbon atoms. 1) Fill in the blank spaces in the table. 2) Draw the structures of these ten unbranched alkanes, using Figure 1 (hexane) as a model. 3) What do the names of these molecules have in common? 4) What is the relationship between the number of carbon atoms and the number of hydrogen atoms in an unbranched alkane? Provide a general formula (use n for the number of carbon atoms). 5) Draw a graph of boiling points versus number of carbon atoms in unbranched alkanes. 6) How do the boiling points vary with the number of carbons? Propose an explanation for this observation. Available for free at Connexions <http://cnx.org/content/col29252/1.3> Chapter 2 Constitutional Isomers 1 Evaluate the two molecules below. Two alkanes Figure 2.1: Two alkanes for comparison How are they the same? How are they dierent? Two molecules which have the same molecular formula but dierent structural formulas, or bonding arrangements, are known as constitutional isomers. Pentane is an alkane with ve carbon atoms. It has three constitutional isomers, shown below. 1 This content is available online at <http://cnx.org/content/m76440/1.1/>. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 3 4 CHAPTER 2. CONSTITUTIONAL ISOMERS Pentane Figure 2.2: Unbranched isomer of pentane Isopentane Figure 2.3: Branched constitutional isomer of pentane Available for free at Connexions <http://cnx.org/content/col29252/1.3> 5 Neopentane Figure 2.4: Branched constitutional isomer of pentane Draw three constitutional isomers of heptane. Circle the constitutional isomers of hexane in the gure below. Why are the remaining molecules not considered to be constitutional isomers of hexane? Figure 2.5 Draw the constitutional isomer of hexane that is missing. What is the minimum number of carbons in the chain of an alkane to be able to have a constitutional isomer? Available for free at Connexions <http://cnx.org/content/col29252/1.3> 6 CHAPTER 2. CONSTITUTIONAL ISOMERS Available for free at Connexions <http://cnx.org/content/col29252/1.3> Chapter 3 Alkyl Substituents 1 An alkane can be appended onto an existing chain to create a branched molecule. This branched piece of substituent. A substituent made from an alkane is called an alkyl group. the molecule is called a Alkyl groups are named similarly to unbranched alkane chains. Alkane Condensed Structure Alkyl Group Condensed Structure Methane CH4 Methyl CH3 - Ethane CH3 CH3 Ethyl CH3 CH2 - Propane CH3 CH2 CH3 Propyl CH3 CH2 CH2 - Butane CH3 CH2 CH2 CH3 Butyl CH3 CH2 CH2 CH2 - Table 3.1 Alkyl groups can also be branched. For example, there are three constitutional isomers of the butyl substituent. In these diagrams, the negative charge on the carbon indicates the site of the bond from the substituent to the rest of the molecule. isobutyl Figure 3.1 1 This content is available online at <http://cnx.org/content/m76443/1.3/>. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 7 8 CHAPTER 3. ALKYL SUBSTITUENTS sec-butyl Figure 3.2 tert-butyl Figure 3.3 When naming molecules according to the IUPAC system of substitutive nomenclature, remember parent-sux (like un-believe-able). prex: what are the substituents? parent: how many carbons in the parent chain? sux: what is the family of compounds? In the case of an alkane, the sux is -ane. prex- The name of this molecule is 2-methylhexane. Identify the alkyl group. Label the parent chain carbons from 1-6. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 9 2-methylhexane Figure 3.4 The name of this molecule is 3-methylheptane. Identify the alkyl group. Label the parent chain carbons from 1-7. 3-methylheptane Figure 3.5 Identify the alkyl group in Molecule A. Label the parent chain carbons from 1-8. What is the name of this molecule? Available for free at Connexions <http://cnx.org/content/col29252/1.3> 10 CHAPTER 3. ALKYL SUBSTITUENTS Identify the alkyl group in Molecule B. Label the parent chain carbons. What is the name of this Molecule A Figure 3.6 molecule? Molecule B Figure 3.7 The name of this molecule is 2,3-dimethylpentane. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 11 2,3-dimethylpentane Figure 3.8 What is the name of Molecule C? Molecule C Figure 3.9 The name of this molecule is 4-ethyl-2-methyloctane. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 12 CHAPTER 3. ALKYL SUBSTITUENTS 4-ethyl-2-methyloctane Figure 3.10 What is the name of Molecule D? Molecule D Figure 3.11 The name of this molecule is 4-isopropylnonane. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 13 4-isopropylnonane Figure 3.12 What is the name of Molecule E? Molecule E Figure 3.13 Available for free at Connexions <http://cnx.org/content/col29252/1.3> 14 CHAPTER 3. ALKYL SUBSTITUENTS The name of this molecule is cyclobutane. cyclobutane Figure 3.14 What is the name of Molecule F? Molecule F Figure 3.15 The name of this molecule is methylcyclobutane. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 15 methylcyclobutane Figure 3.16 The name of this molecule is 1-ethyl-2-methylcyclohexane. 1-ethyl-2-methylcyclohexane Figure 3.17 What is the name of Molecule G? Available for free at Connexions <http://cnx.org/content/col29252/1.3> 16 CHAPTER 3. ALKYL SUBSTITUENTS Molecule G Figure 3.18 Write the steps that you use to name an alkane, in order, as instructions for a student who doesn't know how to do it. Draw any alkane and go through the steps in naming your molecule. Available for free at Connexions <http://cnx.org/content/col29252/1.3> Chapter 4 Alkenes and Alkynes 1 An alkane is a saturated hydrocarbon, meaning that the molecule contains all the possible hydrogen atoms because all the carbon-carbon bonds are single bonds. If one of those carbon-carbon bonds is a double bond, the resulting hydrocarbon is unsaturated and called an alkene. This alkene is named propene. propene Figure 4.1 If one of the carbon-carbon bonds is a triple bond, the resulting hydrocarbon is called an This alkyne is named ethyne. ethyne Figure 4.2 1 This content is available online at <http://cnx.org/content/m76445/1.4/>. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 17 alkyne. 18 CHAPTER 4. ALKENES AND ALKYNES What is the name of Molecule A? Molecule A Figure 4.3 The double or triple bond is called a functional group, and is often the site where chemical reactions occur. Like a substituent, it is specied in the molecular name. When naming molecules according to the IUPAC system of nomenclature, remember prex: what are the substituents? parent: how many carbons? If there prex-parent-sux (like un-believe-able). is a double or triple carbon-carbon bond in the molecule, both carbons in that bond must belong to the parent carbon chain, even if that chain does not have the greatest number of carbons. sux: what is the family of compounds? This molecule is named 2-pentene. 2-pentene Figure 4.4 What is the name of Molecule B? Available for free at Connexions <http://cnx.org/content/col29252/1.3> 19 Molecule B Figure 4.5 What is the name of Molecule C? Molecule C Figure 4.6 This molecule is named 4-methyl-2-pentene. 4-methyl-2-pentene Figure 4.7 What is the name of Molecule D? Available for free at Connexions <http://cnx.org/content/col29252/1.3> 20 CHAPTER 4. ALKENES AND ALKYNES Molecule D Figure 4.8 This molecule is named 3-isobutyl-1-octyne. 3-isobutyl-1-octyne Figure 4.9 What is the name of Molecule E? Available for free at Connexions <http://cnx.org/content/col29252/1.3> 21 Molecule E Figure 4.10 This molecule is named cyclohexene. cyclohexene Figure 4.11 What is the name of Molecule F? Available for free at Connexions <http://cnx.org/content/col29252/1.3> 22 CHAPTER 4. ALKENES AND ALKYNES Molecule F Figure 4.12 This molecule is named 4-methylcyclohexene. Number the carbons. 4-methylcyclohexene Figure 4.13 What is the name of Molecule G? Available for free at Connexions <http://cnx.org/content/col29252/1.3> 23 Molecule G Figure 4.14 This molecule is named 1,3-pentadiene. 1,3-pentadiene Figure 4.15 What is the name of Molecule H? Available for free at Connexions <http://cnx.org/content/col29252/1.3> 24 CHAPTER 4. ALKENES AND ALKYNES Molecule H Figure 4.16 The location of substituents relative to the double bonds can lead to a type of constitutional isomer known as a positional isomer. The name of this molecule is 5-methyl-1,3-cyclohexadiene. 5-methyl-1,3-cyclohexadiene Figure 4.17 What is the name of Molecule I? Available for free at Connexions <http://cnx.org/content/col29252/1.3> 25 Molecule I Figure 4.18 Double or triple carbon-carbon bonds are rigid and planar. Since the carbons cannot rotate freely around the bond, cis/trans isomers are common, and the orientation may be important for chemical reactions. cis-2-butene and trans-2-butene Figure 4.19 Write the steps that you use to name an alkene and an alkyne, in order, as instructions for a student who doesn't know how to do it. Draw any alkene or alkyne and go through the steps in naming your molecule. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 26 CHAPTER 4. ALKENES AND ALKYNES Available for free at Connexions <http://cnx.org/content/col29252/1.3> Chapter 5 Halogens The halogens 1 are elements belonging to Group 7A. Fluorine, chlorine, bromine, and iodine can diatomic forms or when bound to hydrogen as be added to hydrocarbons through reactions with their hydrogen halides. Diatomic halogen vs halogen halide Figure 5.1: where X is any halogen atom When a halogen atom is bound to an otherwise saturated carbon atom, the molecule is known as an alkyl halide. Substituent Symbol Name Fluorine Fl uoro- Chlorine Cl chloro- Bromine Br bromo- Iodine I iodo- Table 5.1 When naming molecules according to the IUPAC system of nomenclature, remember sux (like un-believe-able). prex: what are the substituents? parent: how many carbons? sux: what is the family of compounds? This molecule is named 2-chlorobutane. 1 This content is available online at <http://cnx.org/content/m76446/1.3/>. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 27 prex-parent- 28 CHAPTER 5. 2-chlorobutane Figure 5.2 What is the name of Molecule A? Molecule A Figure 5.3 This molecule is named 2-uoro-3-methylpentane. Available for free at Connexions <http://cnx.org/content/col29252/1.3> HALOGENS 29 2-uoro-3-methylpentane Figure 5.4 This molecule is named 4-iodo-2-methylhexane. 4-iodo-2-methylhexane Figure 5.5 What is the name of Molecule B? Available for free at Connexions <http://cnx.org/content/col29252/1.3> 30 CHAPTER 5. Molecule B Figure 5.6 This molecule is named 1-chloro-2-butene. 1-chloro-2-butene Figure 5.7 This molecule is named 5-uoro-2-hexene. Available for free at Connexions <http://cnx.org/content/col29252/1.3> HALOGENS 31 5-uoro-2-hexene Figure 5.8 What is the name of Molecule C? Molecule C Figure 5.9 This molecule is named 5-uoro-1,3-cyclohexadiene. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 32 CHAPTER 5. HALOGENS 5-uoro-1,3-cyclohexadiene Figure 5.10 What is the name of Molecule D? Molecule D Figure 5.11 Write the steps that you use to name an alkyl halide, in order, as instructions for a student who doesn't know how to do it. Draw any alkyl halide and go through the steps in naming your molecule. Available for free at Connexions <http://cnx.org/content/col29252/1.3> Chapter 6 Benzene and Conjugation 1 Aromatic hydrocarbons, like this benzene ring, have unexpected chemistry. benzene Figure 6.1 We would expect to name this molecule 1,3,5-cyclohexatriene and see its double bonds react like other double bonds. However, these double bonds do not react in the same way as double bonds in a standard alkene. Observe the result of the below experiment under the appropriate reaction conditions. 1 This content is available online at <http://cnx.org/content/m76447/1.2/>. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 33 34 CHAPTER 6. BENZENE AND CONJUGATION Figure 6.2 This surprising stability of the double bonds in the benzene ring is not due to the cyclic arrangement of the carbon chain. Under the appropriate reaction conditions, we see the following results for adding hydrogen across the double bonds of the molecules below. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 35 Figure 6.3 Measuring the bond lengths gives the following result. Bond Type Bond Length (Angstroms) Single 1.54 Double 1.34 Benzene 1.4 Table 6.1 Therefore, the three double bonds of the benzene ring are not true double bonds. The electrons are shared across all of the carbons in the ring, an arrangement called conjugation which is better represented by the below structure. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 36 CHAPTER 6. BENZENE AND CONJUGATION Figure 6.4 When depicting benzene rings using the double bond drawing, remember that the ring is a hybrid between two equally likely resonance structures. Figure 6.5 Therefore both structures below would be named 1-chlorobenzene. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 37 1-chlorobenzene Figure 6.6 When a benzene ring has two substituents, they are named based upon their position to each other rather than by numbers. o-dichlorobenzene Figure 6.7: o is for ortho, with substituents at 1,2 Available for free at Connexions <http://cnx.org/content/col29252/1.3> 38 CHAPTER 6. BENZENE AND CONJUGATION m-chloromethylbenzene Figure 6.8: m is for meta, with substituents at 1,3 p-chlorouorobenzene Figure 6.9: p is for para, with substituents at 1,4 What is the name of Molecule A? Available for free at Connexions <http://cnx.org/content/col29252/1.3> 39 Molecule A Figure 6.10 A benzene ring can be a substituent. The name of this molecule is 2-phenyldecane. 2-phenyldecane Figure 6.11 Available for free at Connexions <http://cnx.org/content/col29252/1.3> 40 CHAPTER 6. BENZENE AND CONJUGATION What is the name of Molecule B? Molecule B Figure 6.12 Conjugation is not limited to cyclic structures. One of the two molecules below does not react with halogen halides under standard reaction conditions. Which molecule do you predict is the more stable one? Why? What prediction would you make about the lengths of its carbon-carbon bonds? Figure 6.13 Write the steps that you use to name a benzene derivative or a molecule containing a benzene ring as a substituent, in order, as instructions for a student who doesn't know how to do it. Draw any benzene-containing molecule and go through the steps in naming your molecule. Available for free at Connexions <http://cnx.org/content/col29252/1.3> Chapter 7 Alcohols 1 In organic chemistry, any alkyl group can be abbreviated as R. An alcohol, in which a hydroxy (-OH) R-OH. group is attached to a carbon of the alkyl group, can be abbreviated as The name of this molecule is ethanol. ethanol Figure 7.1 What is the name of Molecule A? Molecule A Figure 7.2 This molecule is named 2-butanol. 1 This content is available online at <http://cnx.org/content/m76448/1.2/>. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 41 42 CHAPTER 7. 2-butanol Figure 7.3 This molecule is named 6-isopropyl-5-nonanol. Number the carbons. 6-isopropyl-5-nonanol Figure 7.4 Number the carbons. What is the name of Molecule B? Available for free at Connexions <http://cnx.org/content/col29252/1.3> ALCOHOLS 43 Molecule B Figure 7.5 The name of this molecule is 3-propyl-2-octanol. Number the carbons. 3-propyl-2-octanol Figure 7.6 Number the carbons. What is the name of molecule C? Available for free at Connexions <http://cnx.org/content/col29252/1.3> 44 CHAPTER 7. Molecule C Figure 7.7 This molecule is named 3-uorocyclohexanol. Number the carbons. 3-uorocyclohexanol Figure 7.8 Number the carbons. What is the name of Molecule D? Available for free at Connexions <http://cnx.org/content/col29252/1.3> ALCOHOLS 45 Molecule D Figure 7.9 This molecule is named 4-hexen-2-ol. Number the carbons. 4-hexen-2-ol Figure 7.10 Number the carbons. What is the name of Molecule E? Available for free at Connexions <http://cnx.org/content/col29252/1.3> 46 CHAPTER 7. Molecule E Figure 7.11 This molecule is named 2,3-pentanediol. 2,3-pentanediol Figure 7.12 What is the name of Molecule F? Available for free at Connexions <http://cnx.org/content/col29252/1.3> ALCOHOLS 47 Molecule F Figure 7.13 If a hydroxy (-OH) group is attached to an aromatic ring system, it is called a phenol. Two phenols Figure 7.14 This molecule is named 2-chlorophenol or o-chlorophenol. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 48 CHAPTER 7. ALCOHOLS 2-chlorophenol / o-chlorophenol Figure 7.15 Name Molecule G using 1) numbers and 2) the o/m/p nomenclature. Molecule G Figure 7.16 What additions do we make to our existing naming rules to name alcohols? Write the steps that you use to name an alcohol in order, as instructions for a student who doesn't know how to do it. Draw any alcohol and go through the steps in naming your molecule. Available for free at Connexions <http://cnx.org/content/col29252/1.3> Chapter 8 Ethers 1 In organic chemistry, any alkyl group can be abbreviated as R. alkyl groups are linked to the same oxygen, can be abbreviated as An ether, R-O-R. in which the carbons of two This molecule is often referred to simply as ether. Its common name is diethyl ether, and its IUPAC name is ethoxyethane. ethoxyethane Figure 8.1 The common name of this molecule is ethyl methyl ether, and its IUPAC name is methoxyethane. methoxyethane Figure 8.2 1 This content is available online at <http://cnx.org/content/m76568/1.2/>. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 49 50 CHAPTER 8. What are the common and IUPAC names of Molecule A? Molecule A Figure 8.3 The name of this molecule is 2-methoxy-3-methylbutane. Number the carbons. 2-methoxy-3-methylbutane Figure 8.4 Number the carbons. What is the name of Molecule B? Available for free at Connexions <http://cnx.org/content/col29252/1.3> ETHERS 51 Molecule B Figure 8.5 The name of this molecule is 4-butoxy-2-butanol. Number the carbons. 4-butoxy-2-butanol Figure 8.6 Number the carbons. What is the name of Molecule C? Available for free at Connexions <http://cnx.org/content/col29252/1.3> 52 CHAPTER 8. ETHERS Molecule C Figure 8.7 What additions do we make to our existing naming rules to name ethers? Write the steps that you use to name an ether in order, as instructions for a student who doesn't know how to do it. Draw any ether and go through the steps in naming your molecule. Available for free at Connexions <http://cnx.org/content/col29252/1.3> Chapter 9 Aldehydes and Ketones 1 carbonyl group consists of a carbon atom double-bonded to an oxygen atom, written as C=O. Aldehydes and ketones are two compounds which contain the carbonyl group. A aldehyde Figure 9.1: 1 This The R group can also be a hydrogen. content is available online at <http://cnx.org/content/m76583/1.2/>. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 53 54 CHAPTER 9. ALDEHYDES AND KETONES ketone Figure 9.2: Aldehydes The R groups can be the same or dierent. and ketones are constitutional isomers. For example, the aldehyde and ketone below both have the molecular formula C3 H6 O. C3H6O Figure 9.3 The simplest aldehyde is methanal, commonly known as formaldehyde, and used as a preservative. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 55 methanal Figure 9.4 The name of this molecule is butanal. butanal Figure 9.5 What is the name of Molecule A? Available for free at Connexions <http://cnx.org/content/col29252/1.3> 56 CHAPTER 9. ALDEHYDES AND KETONES Molecule A Figure 9.6 This molecule is named 5-methylhexanal. Number the carbons. 5-methylhexanal Figure 9.7 Number the carbons. What is the name of Molecule B? Available for free at Connexions <http://cnx.org/content/col29252/1.3> 57 Molecule B Figure 9.8 This molecule is named 3-ethyl-4-methylhexanal. Number the carbons. 3-ethyl-4-methylhexanal Figure 9.9 Number the carbons. What is the name of Molecule C? Available for free at Connexions <http://cnx.org/content/col29252/1.3> 58 CHAPTER 9. ALDEHYDES AND KETONES Molecule C Figure 9.10 This molecule is named 3-pentenal. Number the carbons. 3-pentenal Figure 9.11 Number the carbons. What is the name of Molecule D? Available for free at Connexions <http://cnx.org/content/col29252/1.3> 59 Molecule D Figure 9.12 A well-known ketone is 2-propanone, commonly known as acetone, and used as a nail polish remover. 2-propanone Figure 9.13 This molecule is named 2-pentanone. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 60 CHAPTER 9. ALDEHYDES AND KETONES 2-pentanone Figure 9.14 What is the name of Molecule E? Molecule E Figure 9.15 The name of this molecule is 5-ethyl-2-heptanone. Number the carbons. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 61 5-ethyl-2-heptanone Figure 9.16 Number the carbons. What is the name of Molecule F? Molecule F Figure 9.17 This molecule is named 6-chloro-4-ethyl-3-heptanone. Number the carbons. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 62 CHAPTER 9. ALDEHYDES AND KETONES 6-chloro-4-ethyl-3-heptanone Figure 9.18 Number the carbons. What is the name of Molecule G? Molecule G Figure 9.19 The name of this molecule is 3-bromocyclohexanone. Number the carbons. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 63 3-bromocyclohexanone Figure 9.20 Number the carbons. What is the name of Molecule H? Molecule H Figure 9.21 The name of this molecule is 4-hydroxy-2-butanone. Number the carbons. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 64 CHAPTER 9. ALDEHYDES AND KETONES 4-hydroxy-2-butanone Figure 9.22 Number the carbons. What is the name of Molecule I? Molecule I Figure 9.23 This molecule is named 5-chloro-4-oxohexanal. Number the carbons. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 65 5-chloro-4-oxohexanal Figure 9.24 Number the carbons. What is the name of Molecule J? Molecule J Figure 9.25 What additions do we make to our existing naming rules to name aldehydes and ketones? Write the steps that you use to name an aldehyde or ketone in order, as instructions for a student who doesn't know how to do it. Draw any aldehyde or ketone and go through the steps in naming your molecule. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 66 CHAPTER 9. ALDEHYDES AND KETONES Available for free at Connexions <http://cnx.org/content/col29252/1.3> Chapter 10 Carboxylic acids and Esters 1 carbonyl group consists of a carbon atom double-bonded to an oxygen atom, written as C=O. When a hydroxy (-OH) group is also bound to the carbonyl carbon, the resulting group is known as a carboxy group. Carboxylic acids contain the carboxy group, and one type of carboxylic acid derivative is an ester. A carboxylic acid Figure 10.1 1 This content is available online at <http://cnx.org/content/m76665/1.2/>. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 67 68 CHAPTER 10. CARBOXYLIC ACIDS AND ESTERS ester Figure 10.2 Carboxylic acids are often abbreviated as R-COOH or R-CO2 H. Some simple carboxylic acids, such as acetic acid and benzoic acid, are referred to primarily by their common names. acetic acid and benzoic acid Figure 10.3 The common name of this molecule is valeric acid. Its formal name is pentanoic acid. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 69 pentanoic acid Figure 10.4 The common name of Molecule A is caprylic acid. What is the formal name of Molecule A? Molecule A Figure 10.5 The name of this molecule is hexanedioic acid. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 70 CHAPTER 10. CARBOXYLIC ACIDS AND ESTERS hexanedioic acid Figure 10.6 What is the name of Molecule B? Molecule B Figure 10.7 The name of this molecule is cyclohexanecarboxylic acid. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 71 cyclohexanecarboxylic acid Figure 10.8 What is the name of Molecule C? Molecule C Figure 10.9 The name of this molecule is 1,2-benzenedicarboxylic acid. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 72 CHAPTER 10. CARBOXYLIC ACIDS AND ESTERS 1,2-benzenedicarboxylic acid Figure 10.10 What is the name of Molecule D? Molecule D Figure 10.11 Available for free at Connexions <http://cnx.org/content/col29252/1.3> 73 The name of this molecule is 4-bromopentanoic acid. Number the carbons. 4-bromopentanoic acid Figure 10.12 Number the carbons. What is the name of Molecule E? Molecule E Figure 10.13 This molecule is named 2-hydroxybutanoic acid (also known as lactic acid). Available for free at Connexions <http://cnx.org/content/col29252/1.3> 74 CHAPTER 10. CARBOXYLIC ACIDS AND ESTERS 2-hydroxybutanoic acid Figure 10.14 What is the name of Molecule F? Molecule F Figure 10.15 This molecule is named 3,6-dioxo-4-hydroxyhexanoic acid. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 75 3,6-dioxo-4-hydroxyhexanoic acid Figure 10.16 What is the name of Molecule G? Molecule G Figure 10.17 Esters are often manufactured to provide fragrance. One example is isobutyl methanoate, which smells like raspberries. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 76 CHAPTER 10. CARBOXYLIC ACIDS AND ESTERS isobutyl methanoate Figure 10.18 The process of esterication involves adding an alcohol to a carboxylic acid in the presence of hydrogen ions. esterication Figure 10.19 To name an ester, rst we name the alcohol used, and then the carboxylic acid. esterication reaction of ethanol and propanoic acid to create ethyl propanoate. Available for free at Connexions <http://cnx.org/content/col29252/1.3> Below is shown the 77 synthesis of ethyl propanoate Figure 10.20 What is the name of Molecule H? Molecule H Figure 10.21 What is the name of Molecule I? Available for free at Connexions <http://cnx.org/content/col29252/1.3> 78 CHAPTER 10. CARBOXYLIC ACIDS AND ESTERS Molecule I Figure 10.22 This molecule is named dimethylbutanedioate. dimethylbutanedioate Figure 10.23 What is the name of Molecule J? Available for free at Connexions <http://cnx.org/content/col29252/1.3> 79 Molecule J Figure 10.24 This molecule is named 2-chloroethyl propanoate. 2-chloroethyl propanoate Figure 10.25 What is the name of Molecule K? Available for free at Connexions <http://cnx.org/content/col29252/1.3> 80 CHAPTER 10. CARBOXYLIC ACIDS AND ESTERS Molecule K Figure 10.26 This molecule is named 2-bromopropyl 4-chlorobutanoate. Number the carbons. 2-bromopropyl 4-chlorobutanoate Figure 10.27 Number the carbons. What is the name of Molecule L? Available for free at Connexions <http://cnx.org/content/col29252/1.3> 81 Molecule L Figure 10.28 What additions do we make to our existing naming rules to name carboxylic acids and esters? Write the steps that you use to name a carboxylic acid in order, as instructions for a student who doesn't know how to do it. Draw any carboxylic acid and go through the steps in naming your molecule. Write the steps that you use to name an ester in order, as instructions for a student who doesn't know how to do it. Draw any ester and go through the steps in naming your molecule. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 82 CHAPTER 10. CARBOXYLIC ACIDS AND ESTERS Available for free at Connexions <http://cnx.org/content/col29252/1.3> Chapter 11 Amines and Amides 1 -NH2 . If the substituted amino group. Amines and amides are two compounds which contain amino or substituted amino groups. Amines are designated as primary, secondary, or tertiary amines based upon the degree of subAn amino group consists of a nitrogen atom bonded to two hydrogen atoms, written as hydrogens are replaced by R groups, the group is referred to as a stitution of the amino group. For example, an amine in which all three of the potential nitrogen bonds are with R groups instead of hydrogens is called a tertiary amine (see the right-most molecule below). primary, secondary, and tertiary amines Figure 11.1 Despite the complexity of the below molecule, because the nitrogen is directly bound to two hydrogens and only one R group, it is a primary amine. 1 This content is available online at <http://cnx.org/content/m76666/1.2/>. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 83 84 CHAPTER 11. AMINES AND AMIDES an enormous primary amine Figure 11.2 There are multiple substitutive nomenclatures for naming amines, with the two most common being IUPAC and Chemical Abstract Service. Both will be described below. This molecule is named 2-pentanamine (CAS) or 2-aminopentane (IUPAC). 2-pentanamine (CAS) / 2-aminopentane (IUPAC) Figure 11.3 What are the names of Molecule A? Available for free at Connexions <http://cnx.org/content/col29252/1.3> 85 Molecule A Figure 11.4 This molecule is named 1,6-hexanediamine (CAS) or 1,6-diaminohexane (IUPAC). 1,6-hexanediamine (CAS) / 1,6-diaminohexane (IUPAC) Figure 11.5 What are the names of Molecule B? Molecule B Figure 11.6 Available for free at Connexions <http://cnx.org/content/col29252/1.3> 86 CHAPTER 11. AMINES AND AMIDES This molecule is named N,N-dimethylethanamine (CAS) or dimethylaminoethane (IUPAC). N,N-dimethylethanamine (CAS) / dimethylaminoethane (IUPAC) Figure 11.7 What are the names of Molecule C? Molecule C Figure 11.8 This molecule is named 4-amino-2-pentanone (CAS) or 4-aminopentan-2-one (IUPAC). Number the carbons. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 87 4-amino-2-pentanone (CAS) / 4-aminopentane-2-one (IUPAC) Figure 11.9 Number the carbons. What are the names of Molecule D? Molecule D Figure 11.10 This molecule is named 2-(N-methylamino)ethanol (CAS) or 2-methylaminoethanol (IUPAC). Number the carbons. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 88 CHAPTER 11. AMINES AND AMIDES 2-(N-methylamino)ethanol (CAS) / 2-methylaminoethanol (IUPAC) Figure 11.11 Number the carbons. What are the names of Molecule E? Molecule E Figure 11.12 an An amide is a carboxylic acid derivative in which the carboxyl -OH has been replaced with amino or substituted amino group. Amides are also described as primary, secondary, or tertiary depending on the number of R groups bound directly to the nitrogen. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 89 primary, secondary, and tertiary amides Figure 11.13 The naming of simple amides is based on the carboxylic acid nomenclature, and keeps the same name in the CAS and IUPAC systems. The name of this molecule is 3-methylbutanamide. 3-methylbutanamide Figure 11.14 What is the name of Molecule F? Available for free at Connexions <http://cnx.org/content/col29252/1.3> 90 CHAPTER 11. AMINES AND AMIDES Molecule F Figure 11.15 The name of this molecule is N-methylbenzamide. N-methylbenzamide Figure 11.16 What is the name of Molecule G? Available for free at Connexions <http://cnx.org/content/col29252/1.3> 91 Molecule G Figure 11.17 What additions do we make to our existing naming rules to name amines and amides, in the substitutive naming system that you use? Write the steps that you use to name an amine in order, as instructions for a student who doesn't know how to do it. Draw any amine and go through the steps in naming your molecule. Write the steps that you use to name an amide in order, as instructions for a student who doesn't know how to do it. Draw any amide and go through the steps in naming your molecule. Available for free at Connexions <http://cnx.org/content/col29252/1.3> 92 INDEX Index of Keywords and Terms Keywords are listed by the section with that keyword (page numbers are in parentheses). Keywords do not necessarily appear in the text of the page. They are merely associated with that section. Ex. apples, 1.1 (1) A Terms are referenced by the page they appear on. acid, 10(67) alcohol, 7(41) aldehyde, 9(53) G H alkane, 1(1), 2(3) alkyne, 4(17) amide, 11(83) amine, 11(83) B C aromatic, 6(33) benzene, 6(33) I K N bond, 4(17) carboxylic, 10(67) 6(33), 7(41), 8(49), 9(53), 10(67), 11(83) conjugation, 6(33) constitutional, 2(3) ester, 10(67) halide, 5(27) halogen, 5(27) hydrocarbon, 1(1) isomer, 2(3) ketone, 9(53) naming, 1(1), 3(7), 4(17), 5(27), 6(33), 7(41), 8(49), 9(53), 10(67), 11(83) 6(33), 7(41), 8(49), 9(53), 10(67), carbonyl, 9(53) double, 4(17) group, 3(7) nomenclature, 1(1), 3(7), 4(17), 5(27), chemistry, 1(1), 3(7), 4(17), 5(27), D E apples, 1 halogenated, 5(27) alkene, 4(17) alkyl, 3(7) Ex. O S T U 11(83) organic, 1(1), 3(7), 4(17), 5(27), 6(33), 7(41), 8(49), 9(53), 10(67), 11(83) saturated, 1(1) substituent, 3(7) triple, 4(17) unbranched, 1(1) ether, 8(49) Available for free at Connexions <http://cnx.org/content/col29252/1.3> 93 ATTRIBUTIONS Attributions Collection: Organic Chemistry Nomenclature Workbook Edited by: Rebekah ODonnell URL: http://cnx.org/content/col29252/1.3/ License: http://creativecommons.org/licenses/by/4.0/ Module: "Unbranched Alkanes" By: Rebekah ODonnell URL: http://cnx.org/content/m76439/1.4/ Pages: 1-2 Copyright: Rebekah ODonnell License: http://creativecommons.org/licenses/by/4.0/ Module: "Constitutional Isomers (Alkanes)" Used here as: "Constitutional Isomers" By: Rebekah ODonnell URL: http://cnx.org/content/m76440/1.1/ Pages: 3-5 Copyright: Rebekah ODonnell License: http://creativecommons.org/licenses/by/4.0/ Module: "Naming Alkyl Substituents" Used here as: "Alkyl Substituents" By: Rebekah ODonnell URL: http://cnx.org/content/m76443/1.3/ Pages: 7-16 Copyright: Rebekah ODonnell License: http://creativecommons.org/licenses/by/4.0/ Module: "4. Alkenes and Alkynes" Used here as: "Alkenes and Alkynes" By: Rebekah ODonnell URL: http://cnx.org/content/m76445/1.4/ Pages: 17-25 Copyright: Rebekah ODonnell License: http://creativecommons.org/licenses/by/4.0/ Module: "5. Halogens" Used here as: "Halogens" By: Rebekah ODonnell URL: http://cnx.org/content/m76446/1.3/ Pages: 27-32 Copyright: Rebekah ODonnell License: http://creativecommons.org/licenses/by/4.0/ Module: "6. Benzene and Conjugation" Used here as: "Benzene and Conjugation" By: Rebekah ODonnell URL: http://cnx.org/content/m76447/1.2/ Pages: 33-40 Copyright: Rebekah ODonnell License: http://creativecommons.org/licenses/by/4.0/ Available for free at Connexions <http://cnx.org/content/col29252/1.3> 94 ATTRIBUTIONS Module: "7. Alcohols" Used here as: "Alcohols" By: Rebekah ODonnell URL: http://cnx.org/content/m76448/1.2/ Pages: 41-48 Copyright: Rebekah ODonnell License: http://creativecommons.org/licenses/by/4.0/ Module: "8. Ethers" Used here as: "Ethers" By: Rebekah ODonnell URL: http://cnx.org/content/m76568/1.2/ Pages: 49-52 Copyright: Rebekah ODonnell License: http://creativecommons.org/licenses/by/4.0/ Module: "9. Aldehydes and Ketones" Used here as: "Aldehydes and Ketones" By: Rebekah ODonnell URL: http://cnx.org/content/m76583/1.2/ Pages: 53-65 Copyright: Rebekah ODonnell License: http://creativecommons.org/licenses/by/4.0/ Module: "10. Carboxylic acids and Esters" Used here as: "Carboxylic acids and Esters" By: Rebekah ODonnell URL: http://cnx.org/content/m76665/1.2/ Pages: 67-81 Copyright: Rebekah ODonnell License: http://creativecommons.org/licenses/by/4.0/ Module: "11. Amines and amides" Used here as: "Amines and Amides" By: Rebekah ODonnell URL: http://cnx.org/content/m76666/1.2/ Pages: 83-91 Copyright: Rebekah ODonnell License: http://creativecommons.org/licenses/by/4.0/ Available for free at Connexions <http://cnx.org/content/col29252/1.3> Organic Chemistry Nomenclature Workbook This workbook guides the student through learning how to name organic chemistry molecules. Through the use of examples, the learner determines the correct nomenclature for each type of molecule. Rules derived by the student through active engagement are easier to remember than rote memorization. About Rhaptos is a web-based collaborative publishing system for educational material.
