145 terms

Chapter 14 Review

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How many valence electrons does O have?
6
How many bonds does O make?
2
either two single bonds (bent structure)
or a double bond
alcohol
an organic compound in which an -OH group is bonded to a saturated carbon atom
What is the functional group of an alcohol?
-OH
the hydroxyl group
When naming alcohols using IUPAC, replace -ane with
-ol
Common naming for alcohols
name the alkyl or cycloalkyl group then add the separate word alcohol
methyl alcohol
common name
ethyl alcohol
common name
propyl alcohol
common name
isopropyl alcohol
common name
1-propanol
2-propanol
t-butyl alchol
common name
2-methyl-2-propanol
5-methyl-2-hexanol
4-methyl-1-hexanol
3-methyl-3-hexanol
2-methyl-3-hexanol
2-bromo-4-methyl-3-hexanol
cyclohexanol
2-methyl-1-propanol
If a double or triple bond is present with an alcohol
the alcohol takes priority
2-propen-1-ol
2-ethyl-1-butanol
2-methyl-4-propyl-4-heptanol
4-methyl-2-pentanol
3-methyl-1-pentanol
3-methyl-2-pentanol
2-methyl-3-pentanol
4-methyl-1-pentanol
cyclopentanol
2-methylcyclopentanol
should have cis/trans but cannot tell from this structure
cyclobutanol
2,3-dichloro-4-methylcyclohexanol
3-methylcyclohexanol
2-ethyl-5-methylcyclohexanol
3-bromocyclohexanol
should be a cis or trans but cannot tell
4-bromocyclohexanol
should be a cis or trans but cannot tell
1,2-ethanediol
1,2-propanediol
1,2,3-propanetriol
2,3-pentanediol
4-methyl-2,3-pentanediol
3,4-hexanediol
2,4-hexanediol
1,8-octanediol
Is methyl pentyl ether an isomer of ethyl propyl ether?
No, they have different molecular formulas.
Is isopropyl propyl ether an isomer of ethoxypropane?
No, they have different molecular formulas.
Is isobutyl methyl ether an isomer of ethyl propyl ether?
Yes
Is sec-butyl ethyl ether an isomer of ethoxypropane?
No, they have different molecular formulas.
Is ethyl propyl ether an isomer of dipropyl ether?
No, they have different molecular formulas.
Is sec-butyl ethyl ether an isomer of dipropyl ether?
Yes
Is butyl isopropyl ether an isomer of dipropyl ether?
No, they have different molecular formulas.
Is propoxypropane an isomer of dipropyl ether?
Yes
R-O-R is the general structure for
ethers
R-O-H is the general structure for
alcohols
Is Ar-O-R an ether?
Yes an ether with one aromatic
Is Ar-O-Ar an ether?
Yes, an ether with two aromatics
1-methoxypropane
IUPAC name
methyl propyl ether
common name
ethyl propyl ether
common name
1-ethoxypropane
IUPAC name
2-ethyoxypropane
IUPAC name
ethyl isopropyl ether
common name
phenoxybenzene
IUPAC name
diphenyl ether
common name
propoxybenzene
IUPAC name
phenyl propyl ether
common name
ethoxybenzene
IUPAC name
ethyl phenyl ether
common name
1-chloro-3-methoxybenzene
IUPAC name
2-ethoxybutane
IUPAC name
sec-butyl ethyl ether
common name
1,3-dimethoxybenzene
IUPAC name
Indicate whether 1-pentanol is an isomer of 1-hexanol.
Not isomers. Different molecular formulas.
1-hexanol C₆H₁₃OH vs 1-pentanol C₅H₁₁OH
Indicate whether 3-hexanol is an isomer of 1-hexanol.
Yes isomers - positional isomers.
Indicate whether 1,3-dimethyl-1-butanol is an isomer of 1-hexanol.
Yes isomers - constitutional isomers (ripped off C and moved to new location)
Indicate whether 2-hexanol is an isomer of 1-hexanol.
Yes isomers - positional isomers.
Give IUPAC names for all isomeric C7 monohydroxy alcohols in which the carbon chain is unbranched.
1-heptanol
2-heptanol
3-heptanol
4-heptanol
Give IUPAC names for all isomeric C8 monohydroxy alcohols in which the carbon chain is unbranched.
1-octanol
2-octanol
3-octanol
4-octanol
For which values of x is the alcohol name 2-methyl-x-pentanol a correct IUPAC name?
x = 1,2,3
For which values of x is the alcohol name 3-methyl-x-pentanol a correct IUPAC name?
x = 1,2,3
Is 2-butanol an isomer of 1-butanol?
Yes, they are positional isomers.
Is 2-methyl-1-propanol an isomer of 1-butanol?
Yes they are constitutional isomers.
Is 2-methyl-2-propanol an isomer of 1-butanol?
Yes they are constitutional isomers.
Is 2-methylcyclopropanol an isomer of 1-butanol?
No, they have different molecular formulas.
Are phenols flammable?
Yes, phenols are flammable
Do phenols undergo dehydration reactions?
Phenols cannot be dehydrated.
Can phenols be oxidized?
Yes, but they require stronger oxidizing agents than 1° and 2° alcohols
Do phenols undergo halogenation?
Phenols do undergo halogenation.
Are phenols acidic or basic?
Phenols are weak acids with Ka values of about 10⁻¹⁰
Dilute (2%) solutions of phenol have long been used as
antiseptics
Phenol derivatives, such as 4-hexylresorcinol, are used in
mouthwashes and throat lozenges.
Phenol derivatives, o-phenylphenol and 2-benzyl-4-chlorophenol are the active ingredients in
Lysol, a disinfectant.
Phenols possess antioxidant activity;
they protect other substances from being oxidized itself in preference to the other substances.
A naturally occurring phenolic antioxidant that is important in the functioning of the human body
vitamin E
Thymol
*obtained from thyme, possesses both flavorant and antibacterial properties
*used in mouthwash
Eugenol
*flavor of cloves
*dentists used clove oil as antiseptic
isoeugenol
odor associated with nutmeg
vanillin
*gives vanilla its flavor
*extracted from dried seed pods of vanilla orchid
*odor can be perceived at extremely low concentrations, but the strength of the odor does not increase greatly as concentration increases.
catechol
derivatives of this compound create the irritating constituents of poison ivy and poison oak
phenol
an organic compound in which an -OH group is attached to a carbon atom that is part of an aromatic carbon ring system.
aryl group
an aromatic carbon ring system from which one hydrogen atom has been removed
3-chlorophenol
2-chlorophenol
4-chlorophenol
o-cresol
m-cresol
p-cresol
m-ethylphenol
3-bromo-4-chlorophenol
Combustion of alcohols
an alcohol reacts with O₂ to produce CO₂ and H₂O
Dehydration reaction
*a chemical reaction in which a water molecule is removed creating an alkene
*the opposite of hydration
*primary alcohols at 180° creates an alkene but at 140° creates an ether
Elimination reaction
a reaction in which two groups or two atoms on neighboring atoms are removed, or eliminated, from a molecule, leaving a multiple bond between the carbon atoms.
Zaitsev's rule
the major product in an intramolecular alcohol dehydration reaction is the alkene that has the greatest number of alkyl groups attached to the carbon atoms of the double bond.
Condensation reaction
a chemical reaction in which two molecules combine to form a larger one while liberating a small molecule, usually water.
A carbon atom in an organic compound is considered oxidized if
it loses hydrogen atoms or gains oxygen atoms in a redox reaction.
A carbon atom in an organic compound is considered reduced if
it gains hydrogen atoms or loses oxygen atoms in a redox reaction.
Possible oxidizing agents
potassium permanganate, KMnO₄
potassium dichromate, K₂Cr₂O₇
chromic acid H₂CrO₄
oxidation of primary alcohol
The molecule loses a H from the hydroxyl group and also off the primary C, creating an aldehyde
oxidation of secondary alcohol
The molecule loses a H from the hydroxyl group and also off the secondary C, creating a ketone
oxidation of a tertiary alcohol
tertiary alcohols do not have H₂ to lose
halogenation of alcohol
*a single product is produced in which the halogen atom is found only where the hydroxyl group was originally located
*heat is required as a catalyst
The general method for preparing alcohols is to
hydrate alkenes
Alkenes reacts with water in the presence of sulfuric acid
to form an alcohol through unsymmetrical addition. Markovnikov's rule applies (H join the H party) is used to determine the predominate alcohol product.
Another method of producing an alcohol is to
add H₂ to a carbonyl group
-ketone = make alcohol with hydroxyl group in the middle of the chain - a 2⁰ alcohol
-aldehyde = make alcohol with hydroxyl group at the end of the chain - a 1⁰ alcohol
primary alcohol
an alcohol in which the hydroxyl-bearing carbon atom is bonded to only one other carbon atom.
secondary alcohol
an alcohol in which the hydroxyl-bearing carbon atom is bonded to two other carbon atom.
tertiary alcohol
an alcohol in which the hydroxyl-bearing carbon atom is bonded to three other carbon atom.
alcohols undergo combustion reactions (+ O₂) to produce
CO₂ + H₂O
Are alcohols polar or nonpolar?
Alcohols have both polar and nonpolar character.
-hydroxyl group is polar
-the alkyl group present is nonpolar
-physical properties depend on what dominates.
-short chain polar, long chain nonpolar
What is the trend for boiling point of straight chained alcohols?
The boiling point increases as the length of the chain increases. More London dispersion forces with increased number of electrons.
How do the boiling points of diols compare to monohydroxyl alcohols?
The boiling point of diols is significantly higher. The additional hydroxyl group increases the number of hydrogen bonds that can be formed.
What state of matter are most alcohols?
Unbranched 1-alcohols and cycloalcohols (1-8 C) are all liquids.
Are 1-alcohols soluble in water?
-That depends on the length of the carbon chain.
-Alcohols with 1 - 3 carbons are completely soluble.
-4-6 carbons slightly soluble
-7+ carbons less than 1 g / 100 mL
Are diols soluble in water?
-Diols are more soluble in water than 1-alcohols
-due to increased hydrogen bonding
-Even diols with up to 7 carbon atoms show appreciable solubility in water
Which have higher boiling points: alkanes or alcohols?
Alcohols! The hydrogen bonds that alcohols can form greatly increases the boiling point of alcohols over alkanes of similar molar mass.
Which are more soluble in water: alkanes or alcohols?
Alcohols! The hydrogen bonds that alcohols can form with water make them soluble while alkanes cannot form hydrogen bonds and thus are insoluble.
about methanol (methyl alcohol)
-colorless liquid
-good fuel for combustion engines (race cars)
-easier fires to put out because soluble in water
-good solvent
-wood alcohol
about ethanol (ethyl alcohol)
-alcohol present in beverages
-produced by fermentation
-oxidizes in liver into acetaldehyde and then into acetic acid
-long-term use = cirrhosis of the liver, loss of memory, physiological addiction
-fetal alcohol syndrome
about isopropyl alcohol (2-propanol)
-marketed as rubbing alcohol
-evaporates easily hence the term - rub on body to relieve high body temperatures
-more toxic than ethanol; however it induces vomiting so doesn't often stay in the body long enough to be toxic
-oxidizes to form acetone
about ethylene glycol (1,2-ethanediol)
-colorless
-odorless
-high boiling point
-miscible with water
-antifreeze for car
-deicer for planes
-poisonous to animals and humans
-oxidizes to form oxalic acid
What is a glycol?
is a diol in which the two hydroxyl groups are on adjacent carbon atoms
about propylene glycol (1,2-propanediol)
-viscous colorless liquid which is nearly odorless but possesses a faintly sweet taste.
-high boiling point
-miscible with water
-antifreeze for cars
-deicer for planes
-poisonous to animals and humans
-oxidizes to form pyruvic acid
about glycerol (1,2,3-propanetriol)
-clear thick liquid about the consistency of honey
-normally present in the body as a product of fat metabolism
-in some Arctic species functions as a biological antifreeze
-great affinity for water vapor
-added to soap and lotions - keep the moisture in
-florists may use on fresh flowers
-lubricative properties make useful for shaving cream
-used to keep sugar from crystallizing in candies and icings
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