SAS9 CHE005 - Carboxylic Acids and Acid Derivatives PDF

Course Code: CHE 005 Lec. SAS Module #9 Name: Class number: _______ Section: ____________ Schedule:...

Course Code: CHE 005 Lec. SAS Module #9 Name: Class number: _______ Section: ____________ Schedule: Date: ______________ ________________________________________ Lesson title: Carboxylic Acids, and Acid Derivatives Materials: Pen and SAS Lesson Objectives: At the end of the lesson, you should be able to: References: 1. write structures of carboxylic acid and acid  H. Stephen Stoker. Exploring derivatives General, Organic, and Biological 2. determine the common and Chemistry (2010). Brooks/Cole, IUPAC names of carboxylic acid and acid Cengage Learning derivatives.  George I. Sackheim, Dennis D. 3. write the chemical reactions that show the Lehman. Chemistry for Health synthesis and preparation of carboxylic acid and Sciences (8th ed.) Pearson Education acid derivatives. Asia Pte.Ltd.  Katherine J. Denniston, Joseph J. Topping, Robert L. Caret. General, Organic and Biochemistry (5th ed.) McGraw-Hill Education (Asia) Productivity Tip: Schedule doing practice drills similar to the ones in this module two or more times this week. Spacing your practice time will help you master the process. A. LESSON PREVIEW/REVIEW Introduction (2 mins) In module 8 we discussed the carbonyl group and two families of compounds-aldehydes and ketones-that contains this group. In this module, we discuss four more families of compounds in which the carbonyl group is present: carboxylic acid, esters, acid chlorides and acid anhydrides. Activity 1: What I Know Chart, part 1 (5 mins) Instructions: “In this chart, reflect on what you know now. Do not worry if you are sure or not sure of your answers. This activity simply serves to get started on thinking about our topic. Answer only the first column, “What I Know”. Leave the third column “What I Learned” blank at this time. What I Know Questions: What I Learned (Activity 4) 1. What are carboxylic acid, ester, acid chlorides and anhydrides? 2. What is an acid derivative? 3. What are the uses of esters? This document is the property of PHINMA EDUCATION  Course Code: CHE 005 Lec. SAS Module #9 Name: Class number: _______ Section: ____________ Schedule: Date: ______________ ________________________________________ B.MAIN LESSON Activity 2: Content Notes (40 mins) CARBOXYLIC ACID Carboxylic Acid is an organic compound whose functional group is the carboxyl group. Carboxyl group is a carbonyl group (C=O) with a hydroxyl group (- OH ) bonded to the carbonyl carbon atom. A general representation for a carboxyl group is: O ║ ⸺ C⸺OH Abbreviated linear designation for the carboxyl group are ⸺COOH and ⸺CO2H The simplest carboxylic acid has a hydrogen atom attached to the carboxyl group carbon atom. O ║ H⸺ C⸺OH Structures for the next two simplest carboxylic acids, those with methyl and ethyl groups, are: O O ║ ║ CH3⸺C⸺OH CH3⸺CH2⸺C⸺OH The structure of the simplest aromatic carboxylic acid involves a benzene ring to which a carboxyl group is attached. O ║ C⸺OH General formulas for carboxylic acids containing alkyl and aryl groups, respectively, are: R⸺COOH and Ar⸺COOH This document is the property of PHINMA EDUCATION  Course Code: CHE 005 Lec. SAS Module #9 Name: Class number: _______ Section: ____________ Schedule: Date: ______________ ________________________________________ NOMENCLATURE FOR CARBOXYLIC ACIDS: Common Nomenclature for Carboxylic Acids: Common names are usually derived from a Latin or Greek word that is related to a source for the acid. Monocarboxylic Acids The common name of monocarboxylic acid is formed by: Rule 1: taking the latin or Greek root name for the specific number of carbon atoms and appending the suffix –- -ic acid. Common names for the first six unbranched monocarboxylic acids Length of Structural formula Latin or Common name Carbon Chain Greek Root C1 monoacid H⸺COOH Form- Formic acid stinging sensation assocaiated with red ant bites is due in part to formic acid ( latin, formica, “ant” C2 monoacid CH2⸺COOH Acet- Acetic acid Gives vinegar its tartness ( sour taste); vinegar contains small amount of acetic acid ( latin, acetum, “sour”) Acetic Acid – is one of the most widely used of all carboxylic acids. Its primary use is an an acidulant – a substance that gives the proper acidic conditions for a chemical reaction. C3 monoacid CH3-CH2⸺COOH Propion- Propionic acid Is the smallest acid that can be obtained from fats ( Greek, protos, “first”, and pion, “fat”) C4 monoacid CH3-(CH2)2⸺COOH Butyr- Butyric acid Rancid butter contains butyric acid (latin, butyrum, “butter”) C5 monoacid CH3-(CH2)3⸺COOH Valer- Valeric acid Found in valerian root (an herb), has a strong odor (latin, valere “to be strong”) C6 mono acid CH3-(CH2)4⸺COOH Capro- Caproic acid The skin secretions of goats contain caproic acid, which contributes to the odor associated with these animals (latin, caper, “goats”) NOTE: that the common and IUPAC naming system for carboxylic acids differ in three ways: 1. the base name for the carbon chain differs. 2. the suffix that ends the name differs, being –ic acid in the common system and –oic acid in the This document is the property of PHINMA EDUCATION  Course Code: CHE 005 Lec. SAS Module #9 Name: Class number: _______ Section: ____________ Schedule: Date: ______________ ________________________________________ IUPAC system. 3. the carbon numbering system differ, involving Greek letters in the common system and Arabic numbers in the IUPAC system. Rule 2: When using common names for carboxylic acids, the positions (locations) of substituents are denoted by using letters of the Geek alphabet rather than numbers. The four letters of the Greek alphabet are: alpha (α ), beta ( β ), gamma (γ), and delta (δ ). The alpha carbon atom is carbon 2, the beta- carbon atom is carbon 3, and so on. Referece: https://www.vecteezy.com/vector-art/89062-free-greek-alphabet-lowercase-vector Example: This document is the property of PHINMA EDUCATION  Course Code: CHE 005 Lec. SAS Module #9 Name: Class number: _______ Section: ____________ Schedule: Date: ______________ ________________________________________ Β-Methylvaleric acid DICARBOXYLIC ACID Common names for the first six unbranched dicarboxylic acids Length of Structural formulas Latin or Common name carbon chain Greek Root C2 diacid HOOC-COOH Oxal- Oxalic acid - The simplest dicarboxylic acid, found in plants of the genus Oxalis, which includes rhubarb and spinach, and in cabbage. Oxalic acid is used to remove rust, bleach straw and leather, and remove ink stains. C3 diacid HOOC-CH2-COOH Malon- Malonic acid C4 diacid HOOC-(CH2)2-COOH Succin- Succinic acid C5 diacid HOOC-(CH2)3-COOH Glutar- Glutaric acid C6 diacid HOOC-(CH2)4-COOH Adip- Adipic acid C7 diacid HOOC-(CH2)5-COOH Pimel- Pimelic acid Dicarboxylic acid Rule 2: The positions of substituents are denoted by using the small Greek alphabet rather than numbers. Example: Α,β-Dimethylsuccinic acid α-Ethyl-γ-methylglutaric acid The contrast between IUPAC names and common names for mono and dicarboxylic acids is as follows: This document is the property of PHINMA EDUCATION  Course Code: CHE 005 Lec. SAS Module #9 Name: Class number: _______ Section: ____________ Schedule: Date: ______________ ________________________________________ The common name prefixes are related to natural sources for the acids. Rule 2: IUPAC NOMENCLATURE FOR CARBOXYLIC ACIDS: IUPAC rules for naming carboxylic acids resemble those for naming aldehydes. Monocarboxylic Acids Is a carboxylic acid in which one carboxyl group is present. IUPAC rules for naming such compounds are: Rule 1: Select as the parent carbon chain the longest carbon chain that includes the carbon atom of the carboxyl group. Rule 2: Name the parent chain by changing the -e ending of the corresponding alkane to -oic acid. Example: Pentane = Pentanoic acid Rule 3: Number the parent chain by assigning the number 1 to the carboxyl carbon atom, but omit this number from the name. Example: Pentanoic acid Rule 4: Determine the identity and location of any substituents in the usual manner, and append this information to the front of the parent chain name. Examples: This document is the property of PHINMA EDUCATION  Course Code: CHE 005 Lec. SAS Module #9 Name: Class number: _______ Section: ____________ Schedule: Date: ______________ ________________________________________ 3-Methylpentanoic acid Pentanoic acid 3-Methyl-butanoic acid 3-Bromo-2-ethylbutanoic acid Rule 5: If the carbonyl group is bonded to a carbon ring, name the ring and add the words carboxylic acid. The carbon bearing the carboxyl group is always carbon 1. Locate any other ring substituent in the usual manner. Examples: Cyclopentanecarboxylic acid 2-Methylcyclpentanecarboxylic acid 4-Choloro-2- mentylcyclohexanecarboxylic acid NOTE: A carboxyl group must occupy a terminal (end) position in a carbon chain because there can be onl y on e oth er bo nd to it. Line-angle structural formulas for the simpler unbranched-chain carboxylic acids: This document is the property of PHINMA EDUCATION  Course Code: CHE 005 Lec. SAS Module #9 Name: Class number: _______ Section: ____________ Schedule: Date: ______________ ________________________________________ IUPAC NOMECLATURE DICARBOXYLIC ACID Is a carboxylic acid that contains two carboxyl groups, one at each end of a carbon chain. Saturated acids of this type are named by: Rule 1: appending the suffix-dioic acid to the corresponding alkane name (the –e is retained to facilitate pronunciation.) Example: Pentane = Pentanedioic acid Rule 2: Both carboxyl carbon atoms must be part of the parent carbon chain, and in carboxyl locations need not be specified with numbers because they will always be at the two ends of the chain. 3-Methylpentanedioic acid 3-Bromohexanedioic acid 2-Ethyl-6-methylheptanedioic acid 5-Bromo-3-chloro-2iodoheptanedioic acid Ruke 3: If 2 carboxyl groups are bonded to a carbon ring, name the ring and add the words dicarboxylic acid. Give the location number of the 2 carboxyl groups. Locate any other ring substituents in the usual manner. Note: if the carboxyl group is more than 2 = tri, tetra, penta….carboxylic acid Examples: This document is the property of PHINMA EDUCATION  Course Code: CHE 005 Lec. SAS Module #9 Name: Class number: _______ Section: ____________ Schedule: Date: ______________ ________________________________________ 1,2-Cyclopentanedicarboxylic acid 3-Methyl-1,2-cyclopentanedicarboxylic acid 2,2-Dimethyl-1,3-cyclopentanedicarboxylic acid IUPAC NOMENCALTURE AROMATIC CARBOXYLIC ACIDS The simplest aromatic carboxylic acid is called benzoic acid. Benzoic acid Other simple aromatic acids are named as derivatives of benzoic acid. 4-Chlorobenzoic acid 3,5-Dichlorobenzoic acid (p-Chlorobenzoic acid) Examples: (aromatic carboxylic acids) Toluic acid This document is the property of PHINMA EDUCATION  Course Code: CHE 005 Lec. SAS Module #9 Name: Class number: _______ Section: ____________ Schedule: Date: ______________ ________________________________________ ORTHO-Toluic acid meta-Toluic acid para-Toluic acid o-Toluic acid m-Toluic acid p-Toluic acid 2-Toluic acid 3-Touic acid 4-Toluic acid Phthalic acid Isophthalic acid Teraphthalic acid 3-Idobenzoic acid 5-Bromoisophthalic acid 3-Nitro-o-toluic acid m-Iodobenzoic acid 3-Nitro-2- toluic acid 3-nitro-2-methylbenzoic acid 2,4-Dimethylbenzoic acid 3,4-Difluoro-2-methylbenzoic acid IUPAC NOMENCLATURE Carboxylic acid Aldehyde Ketone Increasing Priority Alcohol Thiol Alkene Alkyne Alkylthio Alkoxy Equal-priority substituents ( listed in Alkyl alphabetical order) Nitro Halogen Examples: This document is the property of PHINMA EDUCATION  Course Code: CHE 005 Lec. SAS Module #9 Name: Class number: _______ Section: ____________ Schedule: Date: ______________ ________________________________________ 6-Oxohexanoic acid 4,6-Dioxohexanoic acid PHYSICAL PROPERTIES OF CARBOXYLIC ACID Carboxylic acid are polar, both the carbonyl and the hydroxyl part are polar. Very high in melting point and boiling point for carboxylic acid. Unsubstituted saturated monocarboxylic acids containing up to nine carbon atoms are liquids that have strong, sharp odors. Acids with 10 or more carbon atoms in an unbranched chain are waxy solids that are odourless( because of the low volatility). Aromatic carboxylic acids as well as dicarboxylic acids are also odourless solids. PREPARATION OF CARBOXYLIC ACID Oxidation of primary alcohols or aldehydes, using an oxidizing agent (CrO3 or K2Cr2O7) produces carboxylic acids. Aromatic acids can be prepared by oxidizing a carbon side chain( alkyl group ) on a benzene derivative. In this process all the carbon atoms of the alkyl group except the one attached to the ring are lost. The remaining carbon becomes part of the carbonyl group. ESTERS: An ester is a carboxylic acid derivative in which the –OH portion of the carboxyl group has been replaced with an –OR group. The Ester functional group is thus The linear form, the ester functional group can be represented as –COOR or –CO2R. The simplest ester, which has two carbon atoms, has a hydrogen atom attached to the ester functional group. This document is the property of PHINMA EDUCATION  Course Code: CHE 005 Lec. SAS Module #9 Name: Class number: _______ Section: ____________ Schedule: Date: ______________ ________________________________________ NOTE: that the two carbon atoms present are not bonded to each other. There are two or three-carbon esters. The structure of the simplest aromatic ester derived from the structure of benzoic acid, the simplest aromatic carboxylic acid. NOTE: that the difference between a carboxylic acid and an ester is “H versus R” relationship. PREPARATION OF ESTERS Esters are produced through Esterification. An Esterification Reaction is the reaction of a carboxylic acid with an alcohol (or phenol) to produce an ester. A strong acid catalyst (generally H2SO4) is needed for esterification. In the esterification process, a –OH group is lost from the carboxylic acid, a –H atom is lost from the alcohol, and water is formed as a by-product. The net effect of this reaction is substitution of the –OR group of the alcohol for the –OH group of the acid. A specific example of esterification is the reaction of acetic acid with methyl alcohol. Structure of ester in terms of its “parent” alcohol and acid molecules; the ester has an acid part and an alcohol part. This document is the property of PHINMA EDUCATION  Course Code: CHE 005 Lec. SAS Module #9 Name: Class number: _______ Section: ____________ Schedule: Date: ______________ ________________________________________ In this context, it is easy to identify the acid and alcohol from which a given ester can be produced; just add a- OH group to the acid part of the ester and a-H atom to the alcohol part to generate the parent molecules. CYCLIC ESTER (LACTONES) Hydroxy acids compounds which contain both a hydroxyl and a carboxyl group. Cyclic esters are called lactones. A lactones is a cyclic ester. The ring size in a lactone is indicated using a Greek letter. A lactone with a five-membered ring is a γ-lactone and one with a six-membered ring is a δ- lactone. NOMENCLATURE FOR ESTERS IUPAC NOMENCLATURE: Rule 1: The name for the alkyl part of the ester appears first. Followed by a separate word giving the name for the acyl part of the ester. Example: Alkyl part: Methyl Acyl part: Ethanoic acid Methyl ethanoic acid Rule 2: The name for the alkyl part of the ester is simply the name of the R group (alkyl, cycloalkyl, or aryl) present). Example: This document is the property of PHINMA EDUCATION  Course Code: CHE 005 Lec. SAS Module #9 Name: Class number: _______ Section: ____________ Schedule: Date: ______________ ________________________________________ Alkyl part: Methyl Acyl part: Ethanoic acid Methyl ethanoic acid Rule 3: The name for the acyl part of the ester is obtained by dropping the –ic acid ending for the acid’s name and adding the suffix –ate. Examples: Alkyl part: Methyl Acyl part: Ethanoic acid Methyl ethanoic acid Methyl ethanoate Ethyl propanoate Butyl pentanoate Propyl benzoate Alkyl part: Ethyl Acyl part: 2-methylpropanoic acid Propyl 2-chloropentanoate Ethyl 2-methylpropanoic acid Ethy 2-methylpropanoate Ethyl 4-chloro-3-methylbutanoate Ethyl 4-chloro-3,3-dimethylbutanoate Rule 4: In case of diesters, use the suffix -dioate for the acyl part. The ending –e should be retained for pronunciation reason. The alkyl part should be arranged alphabetically Examples: Alkyl part: Dimethyl Acyl part: butanedioic acid Dimethyl butanedioic acid Dimethyl butanedioate This document is the property of PHINMA EDUCATION  Course Code: CHE 005 Lec. SAS Module #9 Name: Class number: _______ Section: ____________ Schedule: Date: ______________ ________________________________________ Alkyl part: Ethyl Acyl part: pentanedioic acid Ethyl propyl pentanedioic acid Ethyl propyl pentanedioate IUPAC NOMENCLATURE Carboxylic acid Ester Acid Halide/Acyl Halide Aldehyde Ketone Increasing Priority Alcohol Thiol Alkene Alkyne Alkylthio Alkoxy Equal-priority substituents ( listed in Alkyl alphabetical order) Nitro Halogen Note: The Ester group will be served as a substituent and be named as “alkoxycarbonyl” group if there is a preence of carboxyl group for carboxylic acid 3-Ethoxy-3-oxopropanoic acid 2-Cyclohexyl-3-ethoxy-3-oxopropanoic acid NOTE: The ester group will be served as a substituent and be named as “alkoxycarbonyl” group if there is a presence of carboxyl group for carboxylic acids. COMMON NOMENCLATURE FOR ESTERS  Common name prefixes. Ending suffix with –ate. Numerical location for substituents in alkyl group. Greek alphabetical location for substituents in acyl group. This document is the property of PHINMA EDUCATION  Course Code: CHE 005 Lec. SAS Module #9 Name: Class number: _______ Section: ____________ Schedule: Date: ______________ ________________________________________ No. of IUPAC NAME COMMON NAME FOR MONOESTER Crabons 1 Methanoate Formate 2 Ethanoate Acetate 3 Propanoate Propionate 4 Butanoate Butyrate 5 Pentanoate Valerate 6 Hexanoate Caproate 7 Hepatanoate Enanthoate 8 Octanoate Caprylate 9 Nonanoate Pelargonate 10 Decanoate Caprate No. of IUPAC NAME COMMON NAME FOR MONOESTER Crabons 2 Ethanedioate Oxalate 3 Propanedioate Malonate 4 Butandioate Succinate 5 Pentanedioate Glutarate 6 Hexanedioate Adipate 7 Octanedioate Pimelate 8 Octanedioate Suberate 9 Nonanedioate Azelaate 10 Decanedioate Sebacate Examples: IUPAC name: 2-Chloroethyl propanoate IUPAC name: Ethyl 2-methylpropanoate Common name: 2- Chloroethyl propionate Common name: Ethyl α-methylpropionate IUPAC name: Methyl 3-oxobutanoate IUPAC name: Dimethyl butanedioate Common name: Methyl β-oxobutyrate Common name: Dimethyl succinate SELECTED COMMON ESTERS This document is the property of PHINMA EDUCATION  Course Code: CHE 005 Lec. SAS Module #9 Name: Class number: _______ Section: ____________ Schedule: Date: ______________ ________________________________________ Esters are responsible for the flavour and fragrance of fruits and flowers, generally, a natural flavour or odor is caused by a mixture of esters, with one particular compound being dominant. The synthetic production of these “dominant” compounds is the basis for the flavoring agents used in ice cream, gelatins, soft drinks and so on. Selected Esters that are Used as Flavoring Agents IUPAC NAME CHARACTERISTIC FLAVOR AND ODOR Isobutyl methanoate Raspberry Propyl ethanoate Pear Pentyl ethanoate Banana Octyl ethanoate Orange Pentyl propanoate Apricot Methyl butanoate Apple Ethyl butanoate Pineapple MEDICATIONS: Numerous esters have medicinal value, including benzocaine ( a local anethetic ), aspirin, and oil of wintergreen ( a counterirritant). Benzocaine salicyclic acid Both aspirin and oil of wintergreen are esters of salicylic acid, an aromatic hydroxyacid. Reaction of acetic acid with the alcohol group of salicylic acid produces aspirin. Reaction of methanol with the acid group of salicylic acid produces oil of wintergreen. Oil of wintergreen, also called methyl salicylate, is used in skin rubs and liniments to help decrease the pain of sore muscles. PHYSICAL PROPERTIES OF ESTERS Ester molecules cannot form hydrogen bonds to each other, because they do not have a hydrogen atom bonded to an oxygen atom. Boiling point of ester are much lower than those of alcohols and carboxylic This document is the property of PHINMA EDUCATION  Course Code: CHE 005 Lec. SAS Module #9 Name: Class number: _______ Section: ____________ Schedule: Date: ______________ ________________________________________ aacids of comparable molecular mass. Solubility rapidly decreases with increasing carbon chain length; borderline solubility situations are reached when three to five carbon atoms are in chain. Low and intermediate- molecular-mass esters arre usually colorless liquids at room temperature. CHEMICAL REACTIONS OF ESTER The most important reaction of esters involves breaking the carbon-oxygen single bond that holds the “alcohol part” and the “acid part” of the ester together. This reaction process is called either ester hydrolysis or ester saponification, depending on reaction conditions. Ester Hydrolysis In ester hydrolysis, an ester reacts with water, producing the carboxylic acid and alcohol from which the ester was formed. Ester Hydrolysis requires the presence of a strong-acid catalyst or enzymes. Ester Saponification A saponification reaction is the hydrolysis of an organic compound, under basic conditions, in which a carboxylic acid salt is one of the products. In ester saponification either NaOH or KOH is used as the base and the saponification products are an alcohol and a carboxylic acid salt. A specific example of ester saponification is: ACID CHLORIDES Is a ccarboxylic acid derivative in which the –OH portion of the carboxyl group has been replaced with a –Cl atom. Thus, acid chlorides have the general formula. This document is the property of PHINMA EDUCATION  Course Code: CHE 005 Lec. SAS Module #9 Name: Class number: _______ Section: ____________ Schedule: Date: ______________ ________________________________________ IUPAC NOMECLATURE OF ACID CHLORIDES Rule 1: Replace the –oic acid ending of the IUPAC name of the parent carboxylic acid with –oyl chloride. Examples: Pentanoic acid Benzoic acid Pentanoyl Chloride 3-Methylpentanoyl chloride Benzoyl chloride Rule 2: In case of cylic acid chlorides, retain the ending –e of the alkane name and adding the suffix word – carbonyl chloride. Cyclohexanecarboxylic acid Cyclohexanecarbonyl chloride 2-Methylcyclohexanecarbonyl chloride Rule 3: For diacid chlorides, the ending –e of the alkane name will be retained adding the word –dioyl chloride. For cyclic diacid chlorides, add the word -dicarbonyl chloride.Note: if more than 2 – use tri, tetra, penta…carbonyl chloride Examples: Butanedioic acid Butanedioyl chloride 6-Chloro-7-iodo-3-methyldecabedioyl chloride 1,2-Cyclobutanedicarboxylic acid 1,2-Cyclobutanedicarbonyl chloride 2-Choloro-4-methyl-1,3,5-cyclohexanetricarbonyl chloride This document is the property of PHINMA EDUCATION  Course Code: CHE 005 Lec. SAS Module #9 Name: Class number: _______ Section: ____________ Schedule: Date: ______________ ________________________________________ IUPAC NOMENCLATURE Carboxylic acid Ester Acid Halide/Acyl Halide Aldehyde Ketone Increasing Priority Alcohol Thiol Alkene Alkyne Alkylthio Alkoxy Equal-priority substituents ( listed in Alkyl alphabetical order) Nitro Halogen Note: The acid halide will be served as a substituent and be named as “halocarbonyl” group if there is a preence of higher priority of functional group Examples: Ethyl 5-Chloro-5-oxopentanoate 6-Chloro-2-methyl-6-oxohexanoiac acid COMMON NOMENCALTUR (ACID CHLORIDE) Rule1: Replace the –ic acid ending of the common name of the parent carboxylic acid with –yl chloride.In comparison to its IUPAC name, replace the –oyl chloride ending with –yl chloride after the common name. Greek alphabetical location for the substituents. # of Carbons IUPAC NAME COMMON NAME for MONOACID CHLORIDES 1 Methanoyl chloride Formyl chloride 2 Ethanol chloride Acetyl chloride 3 Propanoyl chloride Propionyl chloride 4 Butanoyl chloride Butyryl chloride 5 Pentanoyl choride Valeryl chloride 6 Hexanoyl chloride Caproyl chloride 7 Heptanoyl chloride Enanthyl chloride This document is the property of PHINMA EDUCATION  Course Code: CHE 005 Lec. SAS Module #9 Name: Class number: _______ Section: ____________ Schedule: Date: ______________ ________________________________________ 8 Octanoyl chloride Caorylyl chloride 9 Nonanoyl chloride Pelargonyl chloride 10 Decanoyl chloride Capryl chloride # of Carbons IUPAC NAME COMMON NAME for MONOACID CHLORIDES 2 Ethanedioyl chloride Oxalyl chloride 3 Propanedioyl chloride Malonyl chloride 4 Butanedioyl chloride Succinyl chloride 5 Pentanedioyl chloride Glutaryl chloride 6 Hexanedioyl chloride Adipyl chloride 7 Heptanedioyl chloride Pimelyl chloride 8 Octanedioyl chloride Suberyl chloride 9 Nonanedioyl chloride Azelayl chloride 10 Decanedioyl chloride Sebacyl chloride Carboxylic acid Common name: Butyric acid β-Bromopropionic acid IUPAC NAME: Butanoyl Chloride 3-Bromopropanoyl chloride COMMON NAME: Butyryl chloride β-Bromopropionyl chloride Α-Hydroxy-γ-methylvalery chloride IUPAC Name: Butanedioyl chloride Common name: Succinyl chloride ACID ANHYDRIDES An acid anhydride is a carboxylic acid derivative in which the –OH portion of the carboxyl group O ║ has been replaced with a –O-C-R group. Thus, acid anhydrides have the general formula: This document is the property of PHINMA EDUCATION  Course Code: CHE 005 Lec. SAS Module #9 Name: Class number: _______ Section: ____________ Schedule: Date: ______________ ________________________________________ The word anhydride means “without water”. The structure of acid anhydride can be viewed as containing two carbonyl groups joined by a single oxygen atom or, alternatively, as two acyl groups joined by a single oxygen atom. Symmetrical acid anhydrides (both R groups are the same) are named by replacing the acid ending of the parent carboxylic acid name with the word anhydride. Mixed acid anhydride (different R groups present) are named by using the names of the individual parent carboxylic acids ( in alphabetical order ) followed by the word anhydride. IUPAC NOMENCLATURE Carboxylic acid Ester Acid Halide/Acyl Halide Aldehyde Ketone Increasing Priority Alcohol Thiol Alkene Alkyne Alkylthio Alkoxy Equal-priority substituents ( listed in Alkyl alphabetical order) Nitro Halogen This document is the property of PHINMA EDUCATION  Course Code: CHE 005 Lec. SAS Module #9 Name: Class number: _______ Section: ____________ Schedule: Date: ______________ ________________________________________ Note: The acid halide will be served as a substituent and be named as “halocarbonyl” group if there is a preence of higher priority of functional group Activity 3: Skill-building Activities (with answer key) (30 mins. + 5 mins. checking) I: Classify the following compounds as to: A. Carboxylic acid, B. Ester, C. Acid Chloride, D. Acid Anhydride E. Amide. Check your answers against the Keys to Correction found at the last pages of the SAS. Write your score. 1. CH3 CH3 2. CH3CHCH2CHCOOH 3. Br O ║ 4. CH2CHCH2C⸺Cl 5. II: Provide the Common and IUPAC names for each of the following compounds: OH O ║ 1. CH3-CH⸺ C-OH OH O ║ 2. CH3- CH-CH2-C-OH CH3 O ║ 3. CH3 -C-CH2-CH2-C-OH CH3 Cl O ║ 4. CH3-CH2 -C-CH2-C-OH This document is the property of PHINMA EDUCATION  Course Code: CHE 005 Lec. SAS Module #9 Name: Class number: _______ Section: ____________ Schedule: Date: ______________ ________________________________________ Cl O ║ 5. C-OH III: Complete each of the following reactions by supplying the missing product or reagents: O ║ 1. C-Cl + H20 ? O O ║ ║ 2. CH3-C⸺ O⸺ C-CH3 + H2O Heat ? O O ║ ║ 3. CH3-C⸺ OH ? CH3-C⸺ Cl O ║ 4. CH3-CH2-C⸺ OCH2CH3 + H2O H+ Heat ? 5. CH3-CH2-CH2-C-OH + CH3OH H+ Heat ? Activity 4: What I Know Chart, part 2 (3 mins) Instruction: To review what was learned from this session, please go back to Activity 1 and answer the “What I Learned” column. Notice and reflect on any changes in your answers. Activity 5: Check for Understanding (35 mins) I: Assign an IUPAC name to each of the following compounds: O O ║ ║ 1. CH3-C-O- C-CH2-CH2-CH3 O ║ This document is the property of PHINMA EDUCATION  Course Code: CHE 005 Lec. SAS Module #9 Name: Class number: _______ Section: ____________ Schedule: Date: ______________ ________________________________________ 2. CH3-CH2-CH2-CH2-CH2C-Cl O ║ 3. CH3-CH⸺ CH-C-Cl CH3 O O ║ ║ 4. CH3- CH2- CH2-C-O- C⸺ H O ║ 5. CH3- CH2-C-O- CH2-CH3 II- Draw a condensed structural formula for each of the following compounds: 1. Ethyl phenylacetate 2. propionyl chloride 3. 3-Methylbutanoyl chloride 4. butyric anhydride 5. Butanoic ethanoic acid III: Classify the two carboxylic acids in each of the following pairs as: A- both dicarboxylic acid B. both monocarboxylic acid C. one dicarboxylic and one monocarboxylic acid 1. Butyric acid and succinic acid 2. Succinic acid and malonic acid 3. Adipic acid and oxalic acid 4. Caproic acid and formic acid 5. Glutaric and valeric acid C. LESSON WRAP-UP This document is the property of PHINMA EDUCATION  Course Code: CHE 005 Lec. SAS Module #9 Name: Class number: _______ Section: ____________ Schedule: Date: ______________ ________________________________________ Activity 6: Thinking about Learning (5 mins) A. Work Tracker: You are done with this session! Let’s track your progress. Shade the session number you just completed. Reminder: Instructor/Facilitator. Please direct the student to mark their place in the work tracker which is simply a visual to help students track how much work they have accomplished and how much work there is left to do. P1 P2 1 2 3 4 5 6 7 8 9 10 B. Think about your Learning. Tell me what part of the module that you think i need to elaborate further and why? FAQs 1. What is polyfunctional carboxylic acid? Ans. Is a carboxylic acid that contains one or more additional functional groups besides one or more carboxyl groups. Such acids occur naturally in many fruits, are important in the normal functioning of the human body, and find use in over the-counter skin care products and in prescription drugs. 2. How is soap prepared? Ans. Soaps are made from water, a strong base, and natural fats or oils. KEY TO CORRECTIONS for Activity 3: I: Classify the following compounds as to: A. Carboxylic acid, B. Ester, C. Acid Chloride, D. Acid Anhydride E. Amide. Check your answers against the Keys to Correction found at the last pages of the SAS. Write your score. 1. CH3 CH3 2. CH3CHCH2CHCOOH This document is the property of PHINMA EDUCATION  Course Code: CHE 005 Lec. SAS Module #9 Name: Class number: _______ Section: ____________ Schedule: Date: ______________ ________________________________________ 3. Br O ║ 4. CH2CHCH2C⸺Cl 5. Answers: 1. B 2. A 3. E 4. C 5. D II: Provide the Common and IUPAC names for each of the following compounds: OH O ║ 1. IUPAC name: 2-Hydroxypropanoic acid 1. CH3-CH⸺ C-OH Common name: α-Hydroxypropionic acid OH O ║ 2. IUPAC name: 3-Hydroxybutanoic acid 2. CH3- CH-CH2-C-OH Common name: β-Hydroxybutyric acid CH3 O ║ 3. IUPAC name: 4,4-Dimethylpentanoic acid 3. CH3 -C-CH2-CH2-C-OH Common name: γ,γ-Dimethylvaleric acid CH3 Cl O ║ 4. IUPAC name: 3,3-Dichloropentanoic acid 4. CH3-CH2 -C-CH2-C-OH Common name: β,β-Dichlorovaleric acid Cl O ║ 5. IUPAC name: Cyclopentanecarboxylic acid 5. C-OH Commnon name: Cyclovaleric carboxylic acid This document is the property of PHINMA EDUCATION  Course Code: CHE 005 Lec. SAS Module #9 Name: Class number: _______ Section: ____________ Schedule: Date: ______________ ________________________________________ III: Complete each of the following reactions by supplying the missing product or reagents: (Answers) O O ║ ║ 1. C-Cl + H20. C-OH + HCl O O O ║ ║ ║ 2. CH3-C⸺O⸺C-CH3 + H2O Heat 2CH3-C-OH O O ║ ║ 3. CH3-C⸺ OH PCl3, PCl5 or SOCl2 CH3-C⸺Cl O O ║ ║ 4. CH3-CH2-C⸺ OCH2CH3 + H2O H+ Heat CH3-CH2-C-OH + CH3CH20H O O ║ ║ 5. CH3-CH2-CH2-C-OH + CH3OH H+ Heat CH3-CH2-CH2-C-O-CH3 + H20 Citation: https://www.vecteezy.com/vector-art/89062-free-greek-alphabet-lowercase-vector This document is the property of PHINMA EDUCATION