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Chapter 2. Nomenclature

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1. Ionic Bond Nomenclature

2. Covalent Bond Nomenclature

3. Organic Chemistry Nomenclature

4. Linear Alkane Nomenclature

5. Cyclic Alkane Nomenclature

6. Complex Cyclic Alkane Nomenclature

7. Linear Alkene and Alkyne Nomenclature

8. Cyclic Alkene and Alkyne Nomenclature

9. Aromatic Compound Nomenclature

10. Alcohol Nomenclature

11. Ether Nomenclature

12. Epoxide Nomenclature

13. Aldehyde and Ketone Nomenclature

14. Carboxylic Acid and Analogues Nomenclature

15. Amine and Analogues Nomenclature

a. Example of IUPAC Nomenclature

b. Code to determine IUPAC nomenclature from a random molecular structure

1. Ionic Bond Nomenclature

⑴ Nomenclature: Metal ions (including hydrogen) + Nonmetal suffix

① Cation suffix: Generally -ium

○ Example: magnesium, arenium ion

○ When a non-hydrogen metal ion and hydrogen are both present, hydrogen is written later.

② Anion suffix: Generally -ide

○ Exception: Oxygen anions (oxoanions) end with -ate (e.g., glutamate)

⑵ Metal ions

① Transition metals have various oxidation states, so the oxidation state should be indicated in parentheses.

② Iron common names

○ Fe²⁺ = iron (Ⅱ) (IUPAC) = ferrous (common)

○ Fe³⁺ = iron (Ⅲ) (IUPAC) = ferric (common)

③ Copper common names

○ Cu⁺ = copper (Ⅰ) (IUPAC) = cuprous (common)

○ Cu²⁺ = copper (Ⅱ) (IUPAC) = cupric (common)

⑶ Nonmetal suffix

Table 1. Essential Memorization List for Ionic Bond Nomenclature

2. Covalent Bond Nomenclature

⑴ NO: nitrogen monoxide (nickname: nitric oxide)

① Note that it is not mononitrogen monoxide.

⑵ N₂O: dinitrogen monoxide (nickname: nitrous oxide)

⑶ N₂O₅: dinitrogen pentoxide

3. Organic Chemistry Nomenclature

⑴ As the numbers 4, 5, 6, … increase, the higher rule takes precedence.

⑵ Priority of Functional Groups: Higher priority with higher placement

① Carboxyl group (-COOH)

② Acid anhydride

③ Ester group (-COOR)

④ Alkyl halide (-COX)

⑤ Amide group (-CONR2)

⑥ Cyanide group (nitrile) (-CN)

⑦ Aldehyde group (-RCHO)

⑧ Ketone group (-RCOR’)

⑨ Alcohol group (hydroxy group) (-OH)

⑩ Thiol group (-SH)

⑪ Amino group (-NH2)

⑫ Imine group

⑬ Alkene and alkyne: Alkene takes priority if the numbers are the same

⑭ Alkane

⑮ R-O-R’

⑯ R-S-R’

⑰ Halogen group

⑱ Nitro group

⑶ Priority Supplement

① When there are three or more functional groups with different priorities, except for the top one, the rest are considered equal.

○ Example: 3-bromo-5-hydroxybenzaldehyde (Priority: -CHO > -OH = -Br)

② Priority of alkene and alkyne is equal, but if their numbers are the same, alkene takes priority.

⑷ Common Rules

① Main chain selection: Find the main functional group, select the main chain, and treat the rest as substituents (side chains).

② Substituent naming

③ Numbering

○ Higher priority functional groups should have lower numbers.

○ Rule of lower-position priority: If multiple possibilities exist, choose the arrangement where the carbons bearing the functional groups have the smallest possible numbers.

○ Example: 5-ethyl-2,5-dimethylheptane (O)

○ Example: 3-ethyl-3,6-dimethylheptane (X)

○ If numbers are the same, give lower numbers to the earlier functional group in alphabetical order.

○ When there is a functional group with a higher priority than an imino group, the main functional group should be assigned the lowest possible number. Therefore, this rule does not have a significant impact.

○ If numbers are already determined, numbering can be omitted.

○ Example: methylcyclohexene (O)

○ Example: methyl-1-cyclohexene (X)

④ Suffixes

○ If alkenes and alkynes do not affect the main functional group, use only the main functional group as the suffix.

○ Alkenes and alkynes affect the suffix (e.g., enol, yne, -enoic acid).

⑤ Complete name naming

○ Rearrange functional groups of equal priority in alphabetical order.

○ Prefixes like di(2), tri(3), etc., are not considered in alphabetical order.

○ For common names of substituents, consider iso, neo, cyclo, etc., when assigning alphabetical order.

○ For common names of substituents, separations like sec- and tert- are not included in alphabetical order.

○ Name as 《(Substituent position-Substituent name)_n + Main chain + Suffix.》

○ Main chain naming rules

Table 2. Main Chain Naming Rules

⑸ Organic Chemistry Abbreviations

Table 3. Organic Chemistry Abbreviations

4. Linear Alkane Nomenclature

⑴ Main chain selection

① Determine the longest continuous carbon chain as the main chain and treat the remaining as substituents (side chains).

② If there are multiple chains of the same length, choose the one with more side chains as the main chain.

⑵ Substituent naming

① Herein, assume that there are only alkyl groups and halogen groups as substituents, and their priorities are equal.

② Alkyl groups (alkyl): If alkane or cycloalkane acts as a substituent, change -ane to -yl.

○ Alkyl groups based on the number of carbons

Table 4. Alkyl Groups based on the Number of Carbons

○ The carbon nearest to the main chain is labeled as 1.

○ Alkyl groups can be represented as R groups.

○ Some R groups are expressed as abbreviations (e.g., me for methyl group, et for ethyl group, pro for propyl group).

○ alkyl (e.g., ethyl), alkenyl (e.g., ethenyl), alkynyl (e.g., ethynyl) have equal priority

○ Common names: (note) Memorize

○ isopropyl (1-methylethyl)

○ sec -butyl (1-methylpropyl), isobutyl (2-methylpropyl), tert -butyl (1,1-dimethylethyl)

○ isopentyl or isoamyl (3-methylbutyl), neopentyl (2,2-dimethylpropyl)

③ Halogen groups: When a halogen element acts as a substituent, replace with -o.

○ Example: fluoro, chloro, bromo, iodo

④ If the same substituent occurs more than once, add a prefix indicating the number.

○ Example: di(2), tri(3), tetra(4), penta(5), hexa(6)

⑶ Numbering

① Assign sequential numbers to carbons along the main chain from one end to the other.

② When there is one substituent, give the minimum number to the carbon bearing the substituent.

③ When multiple substituents are present, assign numbering such that the lowest number is given to a certain substituent. Even if the sum of the numbers increases significantly, it remains a valid nomenclature.

○ Example: 2,6,6-trimethyloctane (O)

○ Example: 3,3,7-trimethyloctane (X)

④ If numbers are the same, give lower numbers to the substituent attached to the earlier carbon in alphabetical order.

○ Example: 1-bromo-5-chloropentane (O)

○ Example: 1-chloro-5-bromopentane (X)

⑷ Complete Name Naming

① List substituents in alphabetical order.

○ Example: 4-ethyl-3-methyloctane

○ Prefixes like di(2), tri(3), etc., are not considered in alphabetical order.

○ Example: 4-ethyl-2,3-dimethylheptane (O)

○ Example: 2,3-dimethyl-4-ethylheptane (X)

○ Exceptionally, if a substituent has another substituent, include it in the alphabetical order.

○ Example: 7-(2,2-dimethylbutyl)-4-ethyldodecane

○ When using common names of substituents, consider iso, neo, cyclo, etc., when assigning alphabetical order.

○ Example: isopropyl > methyl

○ When using common names of substituents, separations like sec- and tert- are not included in alphabetical order.

○ Example: sec-butyl > ethyl

② Name as 《(Substituent position-Substituent name)_n + Main chain + Suffix.》

○ However, for alkanes, the suffix is -ane.

⑸ For complex substituents, consider one substituent, enclose its name in parentheses, and include it in alphabetical order.

① The part of the substituent adjacent to the main chain is assigned carbon 1.

② Example

○ Example: 4-(2-methylhexyl)octane

○ Example: 7-(2,2-dimethylbutyl)-4-ethyldecane

5. Cyclic Alkane Nomenclature

⑴ Cases with only cycloalkanes

① For cycloalkanes, add “cyclo” in front of the name of the corresponding alkane based on the number of carbons.

② Examples: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane

⑵ Naming the main chain

① According to the existing IUPAC guidelines

○ Case 1: When both acyclic and cyclic alkane structures coexist: Represent the cyclic alkane as a substituent in the following cases:

○ When the substituent has a larger number of carbons

○ When multiple rings are present

○ When neither can be chosen as the parent structure

○ Case 2: When the number of carbons in the acyclic alkane chain and the cyclic alkane are the same, consider the cyclic alkane as the parent structure.

② Latest IUPAC Guidelines: In cases where both ring and chain structures are present, the ring is chosen as the parent structure.

○ Example: octylcyclobutane (preferred)

⑶ When a cyclic alkane is the main chain:

① If there is only one substituent, numbering is not necessary.

○ Example: methylcyclohexane

② When multiple numbering methods are possible, assign numbers so that at least one is the smallest possible number (ref).

○ Example: 1-chloro-2,2,3-trimethylcyclopropane (X), 2-chloro-1,1,3-trimethylcyclopropane (O)

③ When there are two or more substituents, name the substituents, number the positions, and then name the entire molecule.

○ The carbon attached to the substituent that comes first in alphabetical order is numbered 1.

○ Example: 1-ethyl-2-methylcyclopentane

⑷ When an acyclic alkane is the main chain: It is necessary to indicate the number of the cyclic position.

① Example: 1-cyclobutylpentane

6. Complex Cyclic Alkane Nomenclature

⑴ Bicycloalkanes or bridged rings

① Investigate the path from one bridgehead carbon to another.

② Count the number of carbons excluding the bridgehead carbon in each path and write it as [x.y.z] in decreasing order.

③ Numbering:

○ Step 1. Number each carbon starting from one at each bridgehead, following the longest path.

○ Step 2. Number the largest ring first.

Figure 1. Nomenclature of Bicyclic Alkanes

○ Step 3. In cases where multiple possibilities compete, assign numbers such that any carbon with a substituent gets a lower number.

Figure 2. Nomenclature of Bicyclic Alkanes

④ Naming format: 《(substituent position + substituent name)_n + bicyclo[x.y.z]alkane》, where alkane indicates the total number of carbons.

○ Example: 3,3-dimethylbicyclo[3.2.1]octane

⑵ Fused rings (e.g., steroids)

① Investigate the path from one bridgehead carbon to another.

② Count the number of carbons excluding the bridgehead carbon in each path and write it as [x.y.0] in decreasing order.

○ Fused rings have directly connected shared carbons, always represented as z = 0.

③ Numbering: Follow the procedure of ⑴-③.

④ Naming format: 《(substituent position-substituent name)_n + bicyclo[x.y.0]alkane》, where alkane indicates the total number of carbons.

○ Example: 8-methylbicyclo[4.3.0]nonane

⑶ Spiro rings

① Investigate the path from one bridgehead carbon to itself.

② Count the number of carbons excluding the bridgehead carbon in each path and write it as [x.z] in increasing order.

③ Different from bicycloalkanes and fused rings due to not having a bridgehead carbon at 1.

④ Numbering: Follow the procedure of ⑴-③.

⑤ Naming format: 《(substituent position-substituent name)n + bicylo[x.z]alkane》, where alkane indicates the total number of carbons.

○ Example: 1-bromo-3-chlorospiro[4.5]decan-7-ol

7. Linear Alkene and Alkyne Nomenclature

⑴ Choosing the main chain

① Assuming functional groups are only alkyl, halogen, alkene, and alkyne.

② Alkene and alkyne take precedence over alkane, so choose the longest carbon chain containing alkene and alkyne as the main chain and the rest as substituents.

⑵ Substituent naming

① Naming of alkyl and halogen groups is the same as for alkanes.

⑶ Numbering

① Assign sequential numbers to carbons from one end of the main chain to the other.

② Alkenes and alkynes take precedence over substituents, so assign the lowest number to them.

○ Only indicate the position of the first carbon for multiple bonds.

○ Example: 4-methyl-2-pentene

③ When two combinations of numbers are possible, choose the one with the alkene or alkyne having a lower number.

④ When numbers are the same, choose the combination where the alkene (alk e ne) comes before the alkyne (alk y ne) in alphabetical order.

○ Example: 1-penten-4-yne

⑤ When two combinations of numbers are still possible after ④ and there’s only one substituent, assign the number to the carbon with the substituent to minimize its position.

⑥ When two different numbering combinations are possible and there are multiple substituents, assign numbers such that the substituent gets the lowest possible number, even if it means only one carbon has a lower number.

⑦ When numbers are the same after ⑥, assign the smaller number to the one that comes first in alphabetical order.

⑷ Suffix naming

① If there’s only one alkene: Named as 《··· + alkene position-ene》.

② If there’s only one alkyne: Named as 《··· + alkyne position-yne》.

③ If there’s one alkene and one alkyne: Named as 《··· + alkene position-en-alkyne position-yne》.

④ If there’s more than one alkene or alkyne:

○ For alkenes: Change -ene to -diene(2), -triene(3), -tetraene(4), etc., based on the number of alkenes.

○ Example: 4-methyl-1,3-pentadiene

○ For alkynes: Change -yne to -diyne(2), -triyne(3), -tetrayne(4), etc., based on the number of alkynes.

⑸ Complete name naming

① Named as 《(substituent position-substituent name)_n + alk-alkene/alkyne position-suffix》.

② For the alkane part (alk), it should end with a consonant. If there’s a consonant conflict, leave it as -a.

○ Example: hept-1-ene (no -a), hexa-1,3-diene (with -a)

8. Cyclic Alkene and Alkyne Nomenclature

⑴ Choosing the main chain

① When the cyclic alkene or alkyne is attached to an alkane, the cyclic alkene or alkyne takes priority, making it the main chain.

② When the cyclic alkene or alkyne is attached to an acyclic alkene or alkyne

⑵ Substituent naming

① Naming of alkyl and halogen groups is the same as for alkanes.

② If cyclic and acyclic alkenes or alkynes act as substituents, they are named as -enyl or -ynyl instead of -ene or -yne.

○ The carbon closest to the substituent in the main chain is numbered as 1.

⑶ Numbering

① Assign numbers to make the alkene or alkyne between carbons 1 and 2.

② If there are multiple alkenes or alkynes, ensure that ① is followed and assign the lower number to at least one.

③ When numbers are the same, choose the combination where the alkene has a lower number than the alkyne based on alphabetical order.

④ When two numbering combinations are possible (clockwise and counterclockwise) and the substituent is attached to only one carbon of the alkene or alkyne, designate that carbon as 1.

○ Example: 3-ethyl-2-methyl-cyclopent-1-ene (×), 5-ethyl-1-methylcyclopent-1-ene (○)

⑤ When two numbering combinations are possible after ③ and the conditions of ④ are not met, assign the lower number to the carbon with the substituent.

○ When two numbering combinations are possible after ③ and neither is ④:

⑷ Suffix naming: Same as 5 -⑷

① Example: 5-methyl-1,3-cyclohexadiene

⑸ Complete name naming

① Named as 《(substituent position-substituent name)_n + cycloalk-alkene/alkyne position-suffix》.

9. Aromatic Compound Nomenclature

⑴ Substituent naming

⑵ Numbering

① When there’s only one substituent, no separate numbering is assigned.

② Arrange the numbers to make the carbon attached to the higher-priority group (functional group) have the lower number.

○ The highest-priority group gets the number 1.

③ When multiple options are possible, choose the numbering where the carbon attached to the higher-priority group has fewer numbers.

④ Even so, if multiple cases are possible, substituents should be numbered in alphabetical order, giving the lower numbers to the substituents that come first alphabetically.

Figure 3. 1-Bromo-2-chloro-4-ethyl-5-nitrobenzene

⑤ For 1,2-substitution, use ortho(o-); for 1,3-substitution, use meta(m-); for 1,4-substitution, use para(p-).

⑶ Suffix naming: Use common names approved by IUPAC

① When the main functional group is carboxylic acid (-COOH): 《··· + benzoic acid》.

② When the main functional group is aldehyde (-CHO): 《··· + benzaldehyde》.

③ When the main functional group is -COMe: 《··· + acetophenone》.

④ When the main functional group is hydroxyl (-OH): 《··· + phenol》.

⑤ When the main functional group is amino (-NH₂): 《··· + aniline》.

⑥ When the main functional group is ether (-OMe): 《··· + anisol》.

⑦ When the main functional group is methyl (-CH₃): 《··· + toluene》.

⑧ Others: chlorobenzene, styrene, t-butylbenzene, o-xylene, m-xylene, cumene, nitrobenzene, benzonitrile, mesitylene, o-cresol, m-cresol

⑷ Complete name naming

① Alphabetize functional groups with the same priority.

② Named as 《(substituent position-substituent name)_n + main chain + suffix》.

⑸ When benzene ring is treated as a substituent

① When the alkyl substituent has fewer carbons than benzene, treat the alkyl group as the substituent.

② When the alkyl substituent has more or the same number of carbons as benzene, treat benzene as a substituent and represent it as phenyl(= Ph, Φ).

○ Example: 2-phenylhexane (= n-hexylbenzene)

③ When a higher-priority group like a double bond is the main group, treat benzene as a substituent.

⑹ Naming naphthalene, anthracene, and phenanthrene

Figure 4. Naming of naphthalene

Figure 5. Naming of anthracene

Figure 6. Naming of phenanthrene

⑺ Heteroaromatic compound naming

Figure 7. Naming of pyrrole

Figure 8. Naming of imidazole

Figure 9. Naming of furan

Figure 10. Naming of pyridine

Figure 11. Naming of thiophene

Figure 12. Naming of pyrimidine

Figure 13. Naming of quinoline

Figure 14. Naming of isoquinoline

Figure 15. Naming of dibenzo-_p_-dioxin

Figure 16. Naming of azulene

Figure 17. Naming of fluorene

Figure 18. Naming of benzofuran

10. Alcohol Nomenclature

⑴ There are IUPAC rules and common names.

⑵ Naming of alcohols (R-O-H)

① Determine the longest chain or ring containing the alcohol as the main chain.

② Number the carbons of the main chain from the end closest to -OH.

③ Name substituents alphabetically if they are present.

④ Priority order of functional groups when alkenes, alkynes, and alkyl groups are present

○ -OH > alkene > alkyne (when alkene and alkyne have the same number) > halogen

⑤ Common names

○ Example: propyl alcohol, butyl alcohol, sec -butyl alcohol, tert -butyl alcohol, isobutyl alcohol, neopentyl alcohol

⑶ Polyols (polyhydroxy compounds): Naming of compounds with two or more hydroxyl groups

① Add -diol, -triol, etc., to the end of the main chain’s name to indicate the number of hydroxyl groups.

② Assign numbers so that at least one carbon has a lower number, and alphabetically name them.

③ Common names: ethylene glycol (ethane-1,2-diol), glycerol (propane-1,2,3-triol)

11. Ether Nomenclature

⑴ Formal naming

① Use the longest alkane chain as the main chain.

② Name the remaining part as alkoxy.

③ Number the carbons in the main chain where the alkoxy group is attached, starting from 1.

④ If there are substituents on the main chain, name them alphabetically.

○ Example: (3S, 4R)-3-butoxyl-4-methylhexane

⑤ Examples

○ 2-methoxybutane

○ 1-ethoxy-3-methylpentane

○ 1-butoxy-2,3-dimethylpentane

○ 1,4-diisopropoxybutane

⑵ Conventional Nomenclature

① Write the substituent names on both sides of the ether oxygen in alphabetical order, then add the term -ether.

② Examples

○ ethyl methyl ether

○ dietheyl ether (ethyl ether)

○ diphenyl ether

○ tert-butyl isobutyl ether

○ sec-butyl isopropyl ether

○ cyclohexyl isopentyl ether

12. Epoxide Nomenclature

⑴ Oxa type

① Name with a cycloalkane at the end.

② The oxygen forming the ring is numbered as 1.

③ The carbon with the most substituents is assigned the number 2, and in case of equal numbers, alphabetical order is followed.

⑵ Oxirane type

① Name with oxirane at the end.

② The oxygen forming the ring is numbered as 1.

③ The carbon with the most substituents is assigned the number 2, and in case of equal numbers, alphabetical order is followed.

④ Example: 2-methyl-3-phenyloxirane

Figure 19. 2-methyl-3-phenyloxirane

⑶ Epoxyalkane type

① The terminal carbon is assigned the number 1.

② If connected to the 3rd and 4th carbons, named in the form of 3,4-epoxy-.

③ Substituents are named in alphabetical order after numbering.

⑷ Alkene oxide type

① The terminal carbon of the alkene is assigned the number 1 to ensure the lowest numbering.

② Substituents are named in alphabetical order after numbering.

13. Aldehyde and Ketone Nomenclature

⑴ Aldehyde Nomenclature

① The longest chain containing CHO is the parent.

② Aldehyde carbon (CHO) is assigned the number 1.

③ If an aldehyde attached to a ring is the main chain: The suffix is -cycloalkanecarbaldehyde.

④ If an aldehyde in a chain is treated as a substituent: named as oxo.

⑤ If an aldehyde in a ring is treated as a substituent: named as formyl.

⑥ Comparison between the conventional nomenclature (left) and common nomenclature (right).

○ methanal / formaldehyde

○ ethanal / acetaldehyde

○ 2-bromopropanal / α-bromopropionaldehyde

○ 3-chlorobutanal / β-chlorobutyraldehyde

○ 3-methylbutanal / isovaleraldehyde

○ hexandial

⑵ Ketone Nomenclature

① The longest chain containing C=O is the parent.

② The terminal closest to the C=O group is assigned the number 1.

③ If a ketone attached to a ring is the parent: suffix is -cycloalkanone.

④ If a ketone in a chain or ring is treated as a substituent: named as oxo.

⑤ Comparison between the conventional nomenclature (left) and common nomenclature (right).

○ propanone / acetone, dimethyl ketone

○ 3-hexanone / ethyl propyl ketone

○ 6-methyl-2-heptanone / isohexyl methyl ketone

○ 2,4-pentanedione / acetylacetone

○ cyclohexanone /

○ butanedione /

14. Carboxylic Acid and Analogues Nomenclature

⑴ Carboxylic Acid Naming Conventions

① For the end of an alkane, replace -e with -oic acid in naming.

② Formal Naming Rule: The carbon of the -COOH group is designated as carbon 1.

③ Common Naming Rule: The carbon of the -COOH group is designated as α carbon.

④ If there are alkenes, alkynes in the main chain, alkanoic acid becomes like alkenoic acid, alkynoic acid.

Figure 20. propenoic acid와 propynoic acid

⑤ Comparison between Formal Naming Rule (left) and Common Naming Rule (right)

○ methanoic acid / formic acid

○ ethanoic acid / acetic acid

○ propanoic acid / propionic acid

○ butanoic acid / butyric acid

○ pentanoic acid / valeric acid

○ hexanoic acid / caproic acid

○ propenoic acid / acrylic acid

○ 2-methoxybutanoic acid / α-methoxybutyric acid

○ 3-bromopentanoic acid / β-bromovaleric acid

○ 4-chlorohexanoic acid / γ-chlorocaproic acid

⑵ Acyl Chloride Naming Conventions

① When an acyl chloride is the main chain in a ring system, it is named by adding “carbonyl halide” as a suffix to the cycloalkane.

② When an acyl chloride is a substituent in a chain, it is named using the prefix “-oxo” in alphabetical order.

③ When an acyl chloride is a substituent in a ring system, it is named using the prefix “halocarbonyl.”

④ Comparison between Formal Naming Rule (left) and Common Naming Rule (right)

○ ethanoyl chloride / acetyl chloride

○ 3-methylpentanoyl chloride / β-methylvaleryl chloride

⑶ Naming Conventions for Acid Anhydrides

① Remove “acid” from the carboxylic acid and replace with “anhydride” for naming.

② When an acid anhydride is the main chain in a ring system, it is named by adding the suffix “carboxylic anhydride” to the cycloalkane.

③ When an acid anhydride is a substituent in a linear chain, it is named using the prefix “alkanoyloxy-“ or the common name + “oxy.”

④ When an acid anhydride is a substituent in a ring system, it is named using the prefix “alkanoylcarbonyl” or the common name + “carbonyl.”

⑤ For cyclic anhydrides, it is named by adding the suffix “alkanedioic anhydride” to the alkane; however, the common name is frequently used.

⑥ Comparison between Formal Naming Rule (left) and Common Naming Rule (right)

○ ethanoic anhydride / acetic anhydride, symmetrical anhydride

○ ethanoic methanoic anhydride / acetic formic anhydride, mixed anhydride

○ 3-methylbutanoyl 3-methylbutanoate

⑷ Ester Naming Conventions

① Formal Naming Rule: Write the substituent attached to O first, then remove the -ic acid part of the carboxylic acid naming for the main chain and add -ate.

② When an ester is the main chain in a ring system, it is named by adding “carboxylate” to the cycloalkane.

③ When an ester is a substituent in a chain, it is named using “number-alkoxy-number-oxo.”

④ When an ester is a substituent in a ring system, it is named using the prefix “alkoxycarbonyl.”

⑤ Comparison between Formal Naming Rule (left) and Common Naming Rule (right)

○ ethyl ethanoate / ethyl acetate

○ phenyl propanoate / phenyl propionate

○ methyl 3-bromobutanoate / methyl β-bromobutyrate

⑥ Comparison between Formal Naming Rule for Carboxylic Acid Salts (left) and Common Naming Rule (right)

○ sodium methanoate / sodium formate

○ potassium ethanoate / potassium acetate

⑸ Amide Naming Conventions

① Mention the substituent attached to the amide nitrogen first.

○ N-cyclohexylpropanamide

○ N-ethyl-N-methylpentanamide

○ N,N-diethylbutanamide

② Like carboxylic acids, the carbon of C=O becomes carbon 1.

③ If alkyl groups are substituted on N, add N- before the substituent name.

④ When attached to a ring, add carboxamide after cycloalkane for naming.

⑤ When an amide is considered a substituent in a chain, it is named using “number-alkylamino-number-oxo.”

⑥ When an amide is considered a substituent in a ring system, it is named “alkylcarbamoyl.”

⑦ Comparison between Formal Naming Rule (left) and Common Naming Rule (right)

○ ethamide / acetamide

○ 4-chlorobutanamide / γ-chlorobutyramide

⑹ Nitrile Naming Conventions

① When nitrile has the highest priority,the carbon of -CN is carbon 1.

② When a nitrile is the main chain in a ring system, it is named “cycloalkanecarbonitrile.”

③ When a nitrile is a substituent in both chain and ring systems, it is named by adding “cyano-“ as a prefix.

④ Comparison between Formal Naming Rule (left) and Common Naming Rule (right)

○ ethanenitrile / acetonitrile, methyl cyanide

○ 5-methylhexanenitrile / δ-methylcapronitrile, isohexyl cyanide

○ propenenitrile / acrylonitrile

15. Amine and Analogues Nomenclature

⑴ Amine Naming Conventions

① Add “amine” after the name of alkane corresponding to the number of carbons.

② For secondary and tertiary amines, substituents attached to the remaining nitrogen atoms are named by adding “N-“ as a prefix.

③ Amine substituents are indicated with “amino-“.

Input: 2019.02.09 09:51

Modified: 2022.02.04 17:42