Ch. 16 Carboxylic Acids and Esters – Flashcards
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-COOH
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Which functional group is a carboxylic acid?
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-oic acid
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A carboxylic acid is named in the IUPAC system by replacing the -e in the name of the parent alkane with
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What is the common name of the compound below?
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butyric acid
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What is the IUPAC name of the following compound?
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butanoic acid
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In the compound below, the hydroxyl group is in which position as noted by the common system?
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?
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What is the IUPAC name for this compound?
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3-methylbutanoic acid
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What is the method of preparing carboxylic acids from alcohols or aldehydes?
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oxidation
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The structural formula of the carboxylic acid produced by the oxidation of 2,2-dimethyl-1-propanol is
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What kind of intermolecular bonding occurs between carboxylic acids?
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hydrogen bonding
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Why do carboxylic acids have higher boiling points than similar alcohols or aldehydes?
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They form dimers that are relatively stable.
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What happens to water solubility as chain length increases in carboxylic acids?
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it decreases
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Carboxylic acids are __________ than sulfuric acid.
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weaker
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Which of the following is the reaction for the ionization of ?-hydroxypropanoic acid in water?
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sodium formate and H2O
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The neutralization of formic acid by NaOH produces
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Which of the following is the reaction for the neutralization of ?-hydroxybutyric acid with NaOH?
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This functional group is known as a(n)
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ester
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a carboxylic acid and an alcohol
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The reactants that will form an ester in the presence of an acid catalyst are
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ethyl pentanoate
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What is the product of the reaction of pentanoic acid with ethanol in the presence of a strong acid?
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1-propanol and ethanoic acid
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The alcohol and carboxylic acid required to form propyl ethanoate are
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the alcohol
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From what component is the first part of the name of an ester (such as methyl acetate) derived?
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What is the common name of this compound?
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ethyl acetate
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What is the IUPAC name for the following compound?
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ethyl butanoate
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the hydrophobic end
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Which part of a soap is responsible for its ability to dissolve fats and oily dirt?
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1. The parent chain is the longest chain that includes the carbon atom of the carbonyl group 2. Name the parent chain by changing the -e ending of the corresponding alkane name to -al 3. number the parent chain by assigning the #1 to the carbonyl carbon of the aldehyde group but this number is not given in the name 4. Find and number the substituents, always giving the lowest number possible 5. When the aldehyde functional group is attached to a carbon ring, name the ring and add the suffix -carbaldehyde
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Naming Aldehydes
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1. The parent is the longest chain that includes the carbon atom of the carbonyl group 2. Name the parent chain by changing the -e ending of the corresponding alkane name to one 3. Number the parent chain so that the carbonyl carbon receives the lowest possible number - Position of carbonyl carbon is shown by placing the number right before the parent name, like 2-hexanone 4. Find and number the substituents, they go in front of the parent and we always assign the lowest number possible 5. Cyclic ketones are named by giving the name of the carbon ring and adding the suffix -one. We don' t add the #1
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Naming Ketones
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Intermediate between those of alcohols and alkanes of similar molecular mass Have higher boiling points than alkanes because of the dipole-dipole attractions between carbonyl groups in these molecules
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Boiling Points of Aldehydes and Ketones
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Aldehydes and ketones that have 5 carbons or less are soluble in both organic solvents and water Aldehydes and ketones with longer carbon chains are not soluble in water but they are soluble in organic solvents
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Solubility
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Tests to distinguish between aldehydes and ketones -An aqueous solution of AgNO3 (Ag+ is the oxidizing agent) and NH3 is added to the unknown compound. If a silver "mirror" is seen on the inside of the test tube this means you have an aldehyde compound. If you do not see the silver mirror then your compound is (probably) a ketone.
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Tollens Test
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Aldehyde reduction produces a primary alcohol Ketone reduction produces a secondary alcohol
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Reduction of Aldehydes and Ketones
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When H2 is added to an aldehyde a primary alcohol is formed When H2 is added to a ketone a secondary alcohol is formed
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Hydrogenation Reaction
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Turns to Carboxylic Acids. ADD O
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Oxidation of Aldehydes to Form Carboxylic Acids
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Double bond removed from o and h and becomes oh - Primary alcohol. H should be left to oxidise to an acid. Add H2
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Reduction of Aldehydes to Form Primary Alcohols
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Becomes alchohols. Alcohols are OH no double bond . Add H2
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Reduction of Ketones to Form Secondary Alcohols
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Hemiacetal - o-ch3 one and oh replaces double bond. Acetal - two o- ch3
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Addition of Alchohols to Form Hemiacetals and Acetals
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+H20 OH BECOMES O- + H30
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Dissociation of a Carboxylic Acid in Water
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+ NaOH OH becomes C - O- NA+ + H20
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Neutralization of a Carboxylic Acid
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Making an Ester + HO - CH3 CH3 - C - O - CH3
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Esterification: Carboxylic Acid and an Alcohol
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+ H - OH Breaking apart the bond O becomes - OH + HO - CH3
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Acid Hydrolysis of an Ester
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+ NaOH O becomes o- Na+ + HO - CH3
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Base Hydrolysis of an Ester ( Saponification )
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The IUPAC name of a carboxylic acid is obtained by replacing the e in the corresponding alkane name with oic acid.
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Naming Carboxylic Acids
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Step 1 : Write the name for the carbon chain from the alcohol as an alkyl group. Step 2: Change the ic acid of the acid name to ate.
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Naming Esters
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Monosaccharides and Disaccharides
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What are simple sugars?
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Polysaccharides
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What are complex sugars?
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Straight Chain Structure of Glucose
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a-D-Glucose
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Haworth Projections - Cyclc Ring Form of Glucose
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- Right = D isomer - Left = L isomer
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Explain the types of carbohydrate isomer based on their alcohol (OH) group bonded to only or last asymmetric carbon atom
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The OH is drawn up on a ring structure
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Beta-anomer
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The OH is drawn down on a ring structure
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Alpha-anomer
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Straight Chain Structure of Fructose
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D-Glucitol --> D-Glucose --> D-Gluconic Acid
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Oxidation and Reduction of Monosaccharides
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Glucose + Glucose
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Maltose
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Glucose + galactose
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Lactose
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Glucose + Fructose
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Sucrose
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Amylose - a(1-;4) glycosidic bonds Amylopecting a(1-->6) glycosidic bonds or a(1->4) glycosidic bonds
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Starch
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animal starch is a polymer of glucose that is stored in the liver and muscle of animals. a(1-->6) glycosidic bonds or a(1->4) glycosidic bonds.
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Glycogen
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is the major structural material of wood and plants. Humans cannot break down Bcellulose but a cellulose . B(1-->4) GLYCOSIDIC BONDS . Unbranched polysaccharide.
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Cellulose
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aldehyde and 5
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aldopentose
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ketone and 5
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ketopentose
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aldehyde and 6
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aldohexose
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ketone and 6
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ketohexose
