Chapter 5 Carboxylic Acids and Esters
Learn the IUPAC system for naming carboxylic acids and esters. • Learn the derivative of a carboxylic acid in which there is a carbon group connected to ...
Carboxylic Acids Nitriles (CHEM 202)
Naming Substituent Effects on Acidity & Preparing Carboxylic Acids Worksheet such as adding carboxylic acid as the parent name
unit (9) carboxylic acids esters
and amides
Carboxylic Acids A carbonyl with one OH attached is called a
This naming is common practice amongst organic chemists e
Chemistry 234 Chapter 20/21 Problem Set – Answer Key
Nomenclature. 1) Provide the IUPAC name for each of the carboxylic acids below 4) Provide the common name for each of the carboxylic acid derivatives below.
Aldehydes Aldehydes Ketones and Carboxylic Carboxylic Acids
Esters and anhydrides are derivatives of carboxylic acids. The general 8.6 Nomenclature and Structure of Carboxyl Group. Nomenclature and Structure of ...
Chapter 3 Alcohols Phenols
https://www.angelo.edu/faculty/kboudrea/index_2353/Chapter_03_2SPP.pdf
Naming Organic Compounds Practice
A. Identify the class of the following compounds. For any alkanes alkenes
21.1 Introduction Carboxylic Acids
25 Apr 2012 – There are 3 resonance contributors to the acid chloride: 21.7 Reactivity of Carboxylic Acid. Derivatives ... Acid Anhydrides. • Practice with ...
Short Summary of IUPAC Nomenclature of Organic Compounds
Naming Carboxylic Acid Derivatives. The six common groups derived from carboxylic acids are salts anhydrides
unit (9) carboxylic acids esters
and amides
Chapter 5 Carboxylic Acids and Esters
Learn the IUPAC system for naming carboxylic acids and esters. derivative of a carboxylic acid in which there is a carbon group connected to the single- ...
Practice Problems on Carboxylic Acid Derivatives -? Ans 1. For each
Practice Problems on Carboxylic Acid Derivatives -? Ans. 1. For each of the following reaction provide the necessary reagents for the.
Nomenclature of Carboxylic Acids
Learn the IUPAC system for naming carboxylic acids and esters. derivative of a carboxylic acid in which there is a carbon group connected to the single- ...
18H-acid derivatives(P).pptx
Carboxylic acid derivatives will react similar to ketones and aldehydes in The IUPAC naming for these compounds involve naming as alkene-substituted ...
Carboxylic Acids Nitriles (CHEM 202)
Chem 202. Worksheet. Chem 202 Chapter 20 Carboxylic Acids and Nitriles. Naming Substituent Effects on Acidity & Reactions of Carboxylic Acids.
21.1 Introduction Carboxylic Acids 21.1 Introduction Carboxylic
Apr 25 2012 Carboxylic acid derivatives
88 Chapter 20: Carboxylic Acids and Nitriles 20.1 Naming
The nitrile carbon numbered C1. Complex nitriles are named as derivatives of carboxylic acids. Replace -ic acid or -oic acid ending with. -onitrile
Chapter 16: Carboxylic Acids Esters
http://www.chem.latech.edu/~upali/chem121/Notes-C16-121.pdf
Carboxylic acids Carboxylic acid derivatives and Nitriles
Nomenclature of carboxylic acids and their derivatives and nitriles. Nomenclature of carboxylic acids. The IUPAC names of carboxylic acids are obtained by.
[PDF] Carboxylic Acids Nitriles (CHEM 202) - STEM Success Center
Worksheet Chem 202 Chapter 20 Carboxylic Acids and Nitriles Naming Substituent Effects on Acidity Reactions of Carboxylic Acids
Naming Carboxylic Acid Derivatives - Practice Problems
Practice 1 Using the priority of functional groups name each of the following compounds containing a carboxylic acid derivative:
[PDF] Chem 124 PAL Worksheet Carboxylic Acid Derivatives
Give the IUPAC names for the molecules below: Write out the step-by-step mechanism for each reaction below Include all intermediates charges and curved arrows
[PDF] Carboxylic Acid Derivatives Worksheet Name - Laney College
Carboxylic Acid Derivatives Worksheet Name Provide reagents to accomplish each transformation Provide IUPAC names for everything (that you can)
[PDF] Carboxylic acid derivatives practice problems pdf - Squarespace
Carboxylic acid derivatives practice problems pdf esters amides nitriles and also the strategy for naming compounds with multiple functional groups
[PDF] Naming carboxylic acids worksheet - Squarespace
In the previous few posts we have talked about the nomenclature of carboxylic acid derivatives such as acids esters amides nitriles
[PDF] Chapter 5 Carboxylic Acids and Esters - Angelo State University
Learn to recognize the carboxylic acid ester and related functional groups • Learn the IUPAC system for naming carboxylic acids and esters
211: Naming Carboxylic Acid Derivatives - Chemistry LibreTexts
28 jan 2023 · The nomenclature of acid halides starts with the name of the corresponding carboxylic acid If the corresponding carboxylic acid has an –oic
[PDF] Chem 2062 Carboxylic acid and derivative nomenclature worksheet
Carboxylic acid and derivative nomenclature worksheet Write the names for the carboxylic acids shown as well as the related acid chloride (R-COCl)
Chapter 5 Carboxylic Acids and Esters
Mr. Kevin A. Boudreaux
Angelo State University
CHEM 2353 Fundamentals of Organic Chemistry
Organic and Biochemistry for Today (Seager & Slabaugh) www.angelo.edu/faculty/kboudreaChapter Objectives: •Learn to recognize the carboxylic acid, ester, and related functional groups. •Learn the IUPAC system for naming carboxylic acids and esters. •Learn the important physical properties of the carboxylic acids and esters. •Learn the major chemical reaction of carboxylic acids and esters, and learn how to predict the products of ester synthesis and hydrolysis reactions. •Learn some of the important properties of condensation polymers, especially the polyesters.Chapter 5Carboxylic Acids and Esters
2Carboxylic Acids
•Carboxylic acids are weak organic acids which contain the carboxyl group (RCO 2 H): • The tart flavor of sour-tasting foods is often caused by the presence of carboxylic acids.RCOH a carboxylic acid O C O O H the carboxyl groupCOHORCOOH RCO
2 H condensed ways of writing the carboxyl groupChapter 5 Carboxylic Acids and Esters
3Nomenclature of
Carboxylic Acids
4Nomenclature of Carboxylic Acids
• Select the longest carbon chain containing the carboxyl group. The -eending of the parent alkane name is replaced by the suffix -oic acid.
• The carboxyl carbon is always numbered "1" but the number is not included in the name. • Name the substituents attached to the chain in the usual way. • Aromatic carboxylic acids (i.e., with a CO 2 H directly connected to a benzene ring) are named after the parent compound, benzoic acid. C OHOBenzoic acid
Chapter 5 Carboxylic Acids and Esters
5Examples: Naming Carboxylic Acids
• Name the following compounds:HCOHOCH
3 COHO CH 3 CH 2COHOCCH
2 CH 2 CH 3 HOO 6Examples: Naming Carboxylic Acids
• Name the following compounds: CH 3 CHCH 2 COHB rO CH 3 CHCH 2 COH CH 2 CH 2 CH 3 CH 3 O COHO CH 3 CH 2 CHCH 3Chapter 5 Carboxylic Acids and Esters
7Examples: Naming Carboxylic Acids
• Name the following compounds: CH 3 CCH 3 COHO CH 2 CH 2 CHCH 3 CH 3CH C OHOCH
3 8Examples: Naming Carboxylic Acids
• Name the following compounds: COHO CH 3 CH 3 CO 2 H Cl CO OH CH 3 CHCH 3Chapter 5 Carboxylic Acids and Esters
9More Complicated Acids
• For molecules with two carboxylic acid groups the carbon chain in between the two carboxyl groups (including the carboxyl carbons) is used as the longest chain; the suffix -dioic acidis used.
• For molecules with more than two carboxylic acid groups, the carboxyl groups are named as carboxylic acid substituents.
CO HO CO OH ethanedioic acid CCH 2 CO HOO OH propanedioic acid CHCH 2 CH 2 CO CO COOHOHHO
propane-1,2,3-tricarboxylic acid 10Examples: Drawing Carboxylic Acids
• Draw structural formulas for the following molecules: - 2-methylpropanoic acid - 2,2,5-trimethylhexanoic acid - 4,5-dimethyl-3-nitrooctanoic acidChapter 5 Carboxylic Acids and Esters
11Examples: Drawing Carboxylic Acids
• Draw structural formulas for the following molecules: -para-bromobenzoic acid - 2,4,6-trinitrobenzoic acid - 4-ethylpentanedioic acid (what's wrong with this name?) 12Chapter 5 Carboxylic Acids and Esters
13Physical Properties of
Carboxylic Acids
14Physical Properties of Carboxylic Acids
• Carboxylic acids hydrogen bond to themselves to form a dimer: RC OO H RCOH O RC OO H HOH OH H • Carboxylic acids also form hydrogen bonds towater molecules:Chapter 5 Carboxylic Acids and Esters
15Physical Properties of Carboxylic Acids
• Since carboxylic acids can form more than one set of hydrogen bonds, their boiling points are usually higher than those of other molecules of the same molecular weight (MW).
• Low-MW carboxylic acids are generally liquids at room temp. (often, they are somewhat oily); higher-MW carboxylic acids are generally waxy solids.
• Carboxylic acids with 12 to 20 carbon atoms are often referred to as fatty acids, since they are found in the triglycerides in fats and oils (more later).
• Short-chain carboxylic acids are also generally more soluble in water than compounds of similar MW, since they can hydrogen bond to more than one water molecule.
16Physical Properties of Carboxylic Acids
• As the number of carbons in a carboxylic acid series becomes greater, the boiling point increases and the solubility in water decreases.
• Many carboxylic acids that are liquids at room temperature have characteristically sharp or unpleasant odors.
- Ethanoic acid/acetic acid is the main ingredient in vinegar. - Butanoic acid is partially responsible for the odor of locker rooms and unwashed socks. - Hexanoic acid is responsible for the odor of Limburger cheese.• Like most acids, carboxylic acids tend to have a sour taste (e.g., vinegar, citric acid, etc.)
Chapter 5 Carboxylic Acids and Esters
17 Common NameStructural FormulaBP (°C)MP (°C)Solubility (g/100 mL H 2 O)Formic acid H - CO
2H 101 8 Infinite
Acetic acid CH
3 - CO 2H 118 17 Infinite
Propionic acid CH
3 CH 2 - CO 2H 141 -21 Infinite
Butyric acid CH
3 (CH 2 2 - CO 2H 164 -5 Infinite
Valeric acid CH
3 (CH 2 3 - CO 2H 186 -34 5
Caproic acid CH
3 (CH 2 4 - CO 2H 205 -3 1
Caprylic acid CH
3 (CH 2 6 - CO 2H 239 17 Insoluble
Capric acid CH
3 (CH 2 8 - CO 2H 270 32 Insoluble
Lauric acid CH
3 (CH 2 10 - CO 2H 299 44 Insoluble
Myristic acid CH
3 (CH 2 12 - CO 2H Dec. 58 Insoluble
Palmitic acid CH
3 (CH 2 14 - CO 2H Dec. 63 Insoluble
Stearic acid CH
3 (CH 2 16 - CO 2 H Dec. 71 InsolubleTable 5.2Physical properties of some carboxylic acids 18Boiling Points of Various Functional Groups
Figure 5.4
The boiling points of carboxylic acids compared to 1° alcohols, aldehydes and ketones, ethers and alkanes.
Chapter 5 Carboxylic Acids and Esters
19 NameMolecular weightBoiling pointSolubility in waterPentane 72 g/mol 35°C Insoluble
Diethyl ether 74 g/mol 35°C Insoluble
Butanal 72 g/mol 76°C / 100 mL H
2 O1-Butanol 74 g/mol 118°C / 100 mL H
2 OPropanoic acid 74 g/mol 141°C Infinite
Boiling Point:
Carboxylic acid
Alcohols
Aldehydes/Ketones
Ethers
AlkanesWater Solubility:
Carboxylic acid
Alcohols
Aldehydes/Ketones
Ethers
Alkanes
Comparing Physical Properties
20Examples: Predicting Physical Properties
• Arrange the following compounds in order of increasing boiling point. (All of the compounds have about the same molecular weight.)
- 1-pentanol - hexane - butanoic acid -pentanal• Which member of each of the following pairs of compounds would you expect to have a higher solubility in water?
- 2-butanone orpropanoic acid - hexanoic acid orethanoic acidChapter 5 Carboxylic Acids and Esters
21Some Important
Carboxylic Acids
22Important Carboxylic Acids
COMethanoic acid
(Formic acid) (from Latin formica, ant)A component of the venom
of ants and caterpillars; produced in the body when methanol is consumedHOHCOEthanoic acid
(Acetic acid) (from Latin acetum, vinegar)Vinegar is a 5% solution of
acetic acid dissolved in water; acetic acid is also responsible for the taste of sour wine (from the oxidation of ethanol) and sourdough breadCH 3 OH COPropanoic acid
(Propionic acid)Found in Swiss cheese;
salts of this acid are used as mold inhibitorsCH 3 CH 2 OH COButanoic acid
(Butyric acid) (from Latin butyrum, butter)This acid has a foul, rancid odor;
produced from the breakdown of soft triglycerides in butterCH 3 CH 2 CH 2 OHCOHexanoic acid
(Caproic acid)Responsible for the odor of
Limburger cheese.CH
3 CH 2 CH 2 CH 2 CH 2 OHChapter 5 Carboxylic Acids and Esters
23para-Aminobenzoic aid (PABA)
Used in sunscreens; absorbs
short-wavelength UV light. It is also required by bacteria for the production of folic acid, needed to maintain the growth of healthy cell walls; sulfa drugs block the uptake of PABA by bacteria, causing them to be unable to manufacture folic acid, and thus preventing the bacteria from multiplyingOH O H 2 N2-hydroxy-1,2,3-propanetricarboxylic acid
(Citric acid)Found in citrus fruits (lemons, grapefruit,
oranges, etc.); commonly used in buffering solutions with sodium citrateOH OHO HOO OHOOxalic acid
Found in many leafy green plants
such as rhubarb and spinach; combines with calcium ions in the body to produce insoluble salts, which form kidney stonesHO O OHOTerephthalic acid
A white, crystalline solid; used in
the manufacture of some polyestersOH O HOO 24Glycolic acid
An alpha-hydroxy acid used in
cosmetics and skin creams; alpha-hydroxy acids are thought to loosen the cells of the epidermis and accelerate the flaking off of dead skin; however these compounds can increase the skin's sensitivity to UV lightO OH HO2-hydroxypropanoic acid
(Lactic acid)Produced from the fermentation of sugars
under anaerobic conditions; found in sweat, sour milk, fermented pickles, sauerkraut, and yogurt; produced in muscles from glucose under anaerobic conditions (the buildup of lactic acid leads to a heavy, weak feeling, and muscle cramps); produced after death during the breakdown of sugars in the body by bacteria, inactivating the enzymes that allow the transport of calcium ions, causing rigor mortisOH O OHMalic acid
Responsible for the sharp
taste of apples (genus Malus)OHO OH HO OChapter 5 Carboxylic Acids and Esters
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