Chemistry: Chapter 23: Functional Groups
Terms in this set (59)
a specific arrangement of atoms in an organic compound that is capable of characteristic chemical reactions
Example: In a ketone, the functional group is the C=O bond
How are organic compounds classified?
According to their functional groups
a class of organic compounds containing covalently bonded fluorine, chlorine, bromine, or iodine (i.e., a halogen)
What are the IUPAC rules for naming halocarbons?
The halogen substituent is the prefix, followed by the name of the parent molecule
CH3-Cl is Chloromethane
Halocarbons in which a halogen is attached to a carbon of an aliphatic chain
halocarbons in which a halogen is attached to a carbon of an arene ring
How does halogenation affect the boiling point and intermolecular forces of a halide?
As halogenation increases, so does the boiling point and the strength of the dipole-dipole interactions
Example: CH4 has a lower boiling point than CH3Cl, which has a lower boiling point than CCl4
An organic compound with a hydroxyl group
An alcohol in which the -OH group is attached to a carbon that is attached to only 1 other carbon
An alcohol in which the -OH group is attached to a carbon that is attached to 2 other carbons
An alcohol in which the -OH group is attached to a carbon that is attached to 3 other carbons
How does solubility of alcohols vary as you increase the number of carbons?
Increasing the number of carbons (beyond 4) decreases the solubility of alcohols.
The more carbons, the more nonpolar bonds there are in the molecule overall, and the lower the concentration of hydrogen bonds among the molecules.
The production of ethanol from sugars by the action of yeast or bacteria.
Ethanol with an added substance to make it toxic (poisonous).
a substance is added at the double or triple bond of an alkene or alkyne
Introduces new functional groups to organic molecules
the addition of water to an alkene
Requires acid and heat (100 degrees celsius)
the addition of hydrogen to a carbon-carbon double bond to produce an alkane
Requires a catalyst: Platinum (Pt) or palladium (Pd)
What's the IUPAC system for naming alcohols?
Take the alkane name and replace the -e with -ol
If there is more than one -OH group, add a prefix (diol, triol, tetrol, etc.)
A compound that has an oxygen attached to two carbon groups
An ether attached to two identical carbon groups
Example: diethyl ether
An ether attached to two different groups
Example: Ethyl methyl ether
A functional group with structure C=O
Found in aldehydes and ketones
an organic compound in which the carbon of the carbonyl group is always joined to at least 1 hydrogen
General formula: RCHO
Examples: Cinnamaldehyde, Vanillin
An organic compound in which the carbon of the carbonyl group is joined to two other carbons
General formula: RCOR
A compound with a carboxyl group (-COOH), which has a carbonyl attached to a hydroxyl group
General formula: RCOOH
Why are carboxylic acids considered acids?
They ionize slightly in solution to create a carboxylate ion + hydrogen ion
Continuous-chain carboxylic acids isolated from fats
How do the boiling points of carboxylic acids compare with those of other organic compounds?
Carboxylic acids have the highest melting and boiling points of organic compounds; each molecule can experience two hydrogen bonds, which is higher than any other category of molecule
What is the solubility of carboxylic acids?
1) 1-4 carbons are miscible with water
2) 5+ carbons has low solubility (nonpolar alkane tail makes molecule more nonpolar)
Contain a carbonyl group and an ether link to the carbonyl carbon
General formula: RCOOR
Examples: various fruit odors (blueberries, pineapples, apples, etc.)
What is the solubility of esters?
1) 1-4 carbons, limited solubility in water (no hydrogen bonding)
2) 5+ carbons, very limited solubility
The reaction of a carboxylic acid and an alcohol to form an ester (using mineral acid as a catalyst)
If you heat an ester in a strong acid or base solution, it decomposes into a carboxylic acid and an alcohol
How do you determine the degree of oxidation/reduction of an organic compound?
1) Fewer hydrogens = more oxidized
Example: alkynes > alkenes > alkanes in oxidation
2) More oxygens = more oxidized
Example: CO2 > HCOOH > HCOH > CH3OH > CH4 in oxidation
What molecule can you make by oxidizing a primary alcohol?
What molecule can you make by oxidizing an aldehyde?
A carboxylic acid
This reaction happens very easily, so if you want to isolate an aldehyde when you're oxidizing a primary alcohol, you need to remove it quickly before it becomes a carboxylic acid
What molecule can you make by oxidizing a secondary alcohol?
Primary alkyl group
When the first carbon on the alkyl group is bonded to only 1 carbon
Secondary alkyl group
When the first carbon on the alkyl group is bonded to 2 carbons
Tertiary alkyl group
When the first carbon on the alkyl group is bonded to 3 carbons
Alkene alkyl group
Benzene alkyl group
A reaction in which an atom, or group of atoms, is replaced with a different atom or group of atoms.
What happens when you mix a halogen with an alkane?
The halogen can replace a hydrogen atom on the alkane to produce a halocarbon
What happens when you treat a benzene with a halogen?
The halogen can replace a hydrogen atom on benzene
What happens when you treat a halocarbon with hydroxide ions?
The halogen is replaced by the OH group, creating an alcohol and halogen ion
What is the IUPAC system for naming aldehydes?
Find the alkane name, and replace the -e with -al
Example: Butane --> butanal
What is the IUPAC system for naming ketones?
Find the alkane name, and replace the -e with -one
Example: Propane --> Propanone
What is the solubility of aldehydes and ketones?
1) 1-6 carbons can dissolve in water (the carbonyl group can hydrogen bond with water)
2) All aldehydes and ketones can dissolve in nonpolar solvents (carbon-hydrogen bonds are nonpolar)
How do the boiling points of aldehydes and ketones compare with those of alcohols and alkanes?
1) Aldehydes and ketones have lower boiling points than those of alcohols because they cannot form intermolecular hydrogen bonds; there are no -OH groups
2) They have higher boiling points than those of alkanes because there are dipole-dipole intermolecular forces of attraction among the molecules
The loss of hydrogen
Usually requires strong heat and a catalyst
Is dehydrogenation reaction considered an oxidation or reduction reaction?
Oxidation, because it involves the loss of 2 electrons
a large molecule formed by the covalent bonding of repeating smaller molecules
The smaller molecules that combine to form a polymer
How does an addition polymer form?
When unsaturated monomers react to polymerize
How do the physical properties of polymers change as you increase the length of the polymers?
Longer polymers typically have harder and more rigid consistencies (higher melting point due to more London Dispersion forces)
Formed by head-to-tail joining of monomer units. Each monomer must have a functional group on the head and tail to be part of the chain
Usually accompanied by the formation of water
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