Ch. 16 Carboxylic Acids and Esters

Flashcard maker : Tyree Bender
Which functional group is a carboxylic acid?
-COOH
A carboxylic acid is named in the IUPAC system by replacing the -e in the name of the parent alkane with
-oic acid
butyric acid
What is the common name of the compound below?
butanoic acid
butanoic acid
What is the IUPAC name of the following compound?
α
α
In the compound below, the hydroxyl group is in which position as noted by the common system?
3-methylbutanoic acid
3-methylbutanoic acid
What is the IUPAC name for this compound?
oxidation
What is the method of preparing carboxylic acids from alcohols or aldehydes?
The structural formula of the carboxylic acid produced by the oxidation of 2,2-dimethyl-1-propanol is
The structural formula of the carboxylic acid produced by the oxidation of 2,2-dimethyl-1-propanol is
hydrogen bonding
What kind of intermolecular bonding occurs between carboxylic acids?
They form dimers that are relatively stable.
Why do carboxylic acids have higher boiling points than similar alcohols or aldehydes?
it decreases
What happens to water solubility as chain length increases in carboxylic acids?
weaker
Carboxylic acids are __________ than sulfuric acid.
Which of the following is the reaction for the ionization of β-hydroxypropanoic acid in water?
Which of the following is the reaction for the ionization of β-hydroxypropanoic acid in water?
The neutralization of formic acid by NaOH produces
sodium formate and H2O
Which of the following is the reaction for the neutralization of β-hydroxybutyric acid with NaOH?
Which of the following is the reaction for the neutralization of β-hydroxybutyric acid with NaOH?
ester
ester
This functional group is known as a(n)
The reactants that will form an ester in the presence of an acid catalyst are
a carboxylic acid and an alcohol
What is the product of the reaction of pentanoic acid with ethanol in the presence of a strong acid?
ethyl pentanoate
The alcohol and carboxylic acid required to form propyl ethanoate are
1-propanol and ethanoic acid
From what component is the first part of the name of an ester (such as methyl acetate) derived?
the alcohol
ethyl acetate
What is the common name of this compound?
ethyl butanoate
ethyl butanoate
What is the IUPAC name for the following compound?
Which of the following is the reaction for the acid hydrolysis of ethyl formate (ethyl methanoate)?
Which of the following is the reaction for the saponification (base hydrolysis) of methyl acetate (methyl ethanoate)?
Which part of a soap is responsible for its ability to dissolve fats and oily dirt?
the hydrophobic end
Naming Aldehydes
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
Naming Ketones
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
Boiling Points of Aldehydes and Ketones
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
Solubility
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
Tollens Test
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.
Reduction of Aldehydes and Ketones
Aldehyde reduction produces a primary alcohol
Ketone reduction produces a secondary alcohol
Hydrogenation Reaction
When H2 is added to an aldehyde a primary alcohol is formed
When H2 is added to a ketone a secondary alcohol is formed
Oxidation of Aldehydes to Form Carboxylic Acids
Turns to Carboxylic Acids. ADD O
Reduction of Aldehydes to Form Primary Alcohols
Double bond removed from o and h and becomes oh – Primary alcohol. H should be left to oxidise to an acid. Add H2
Reduction of Ketones to Form Secondary Alcohols
Becomes alchohols. Alcohols are OH no double bond . Add H2
Addition of Alchohols to Form Hemiacetals and Acetals
Hemiacetal – o-ch3 one and oh replaces double bond.
Acetal – two o- ch3
Dissociation of a Carboxylic Acid in Water
+H20
OH BECOMES
O- + H30
Neutralization of a Carboxylic Acid
+ NaOH
OH becomes
C – O- NA+ + H20
Esterification: Carboxylic Acid and an Alcohol
Making an Ester
+ HO – CH3
CH3 – C – O – CH3
Acid Hydrolysis of an Ester
+ H – OH
Breaking apart the bond
O becomes
– OH + HO – CH3
Base Hydrolysis of an Ester ( Saponification )
+ NaOH
O becomes
o- Na+ + HO – CH3
Naming Carboxylic Acids
The IUPAC name of a carboxylic acid is obtained by replacing the e in the corresponding alkane name with oic acid.
Naming Esters
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.
What are simple sugars?
Monosaccharides and Disaccharides
What are complex sugars?
Polysaccharides
Straight Chain Structure of Glucose
Straight Chain Structure of Glucose
Haworth Projections – Cyclc Ring Form of Glucose
a-D-Glucose
Straight Chain Structure of Galactose
Explain the types of carbohydrate isomer based on their alcohol (OH) group bonded to only or last asymmetric carbon atom
– Right = D isomer
– Left = L isomer
Beta-anomer
The OH is drawn up on a ring structure
Alpha-anomer
The OH is drawn down on a ring structure
Straight Chain Structure of Fructose
Straight Chain Structure of Fructose
Oxidation and Reduction of Monosaccharides
D-Glucitol –> D-Glucose –> D-Gluconic Acid
Maltose
Glucose + Glucose
Lactose
Glucose + galactose
Sucrose
Glucose + Fructose
Starch
Amylose – a(1->4) glycosidic bonds
Amylopecting a(1–>6) glycosidic bonds or a(1->4) glycosidic bonds
Glycogen
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.
Cellulose
is the major structural material of wood and plants. Humans cannot break down Bcellulose but a cellulose . B(1–>4) GLYCOSIDIC BONDS .
Unbranched polysaccharide.
aldopentose
aldehyde and 5
ketopentose
ketone and 5
aldohexose
aldehyde and 6
ketohexose
ketone and 6

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