61 Questions
Which group is bonded directly to a $sp^3$ hybrid carbon atom in alcohols?
Hydroxyl group
How is ethanol commonly produced?
Natural fermentation of sugars and starch
What byproducts are formed during the fermentation process to produce ethanol?
Ethanol and carbon dioxide
What is the modern method of producing methanol?
Catalytic reduction of carbon monoxide by hydrogen gas
Which term describes alcohols with straight or branched chain hydrocarbons?
Aliphatic hydroxyl compounds
Which of the following is an example of a 2° alcohol?
2-propanol
What is the correct IUPAC name for 2-propanol?
propan-2-ol
In the IUPAC naming system, what is done to the name of the parent alkane when naming alcohols?
All of the above
Which of the following is NOT true about 3° alcohols?
They have a primary hydrogens
Which IUPAC rule is used to select the parent structure in alcohol naming?
Select the longest continuous chain containing the -OH group
Which statement is correct for 2-Methyl-2-butanol?
It is a 3° alcohol.
How are substituents named when a compound contains more than one substituent?
Alphabetically before the alcohol name
What functional group does an alcohol contain?
Hydroxyl group
Which of the following compounds is named 1-Propanol?
CH3CH2CH2OH
What is the IUPAC name for the compound CH3CCCHCH2CHCH2OH?
4-Bromo-2-Chloro-5-heptyn-1-ol
How does the number of carbon atoms affect the solubility of alcohols in water?
Solubility decreases with an increasing number of carbon atoms
Which of these compounds is most likely to dissolve in water?
Methanol (CH3OH)
What effect does the hydroxyl group have on the boiling point of alcohols?
Increases the boiling point
What is the correct IUPAC name for the compound HOCH2CH2OH?
1,2-Ethanediol
What is methanol used as in jets?
Additive to jet fuels
A primary alcohol has how many alkyl groups bonded to the sp³ hybrid carbon atom?
One
What is the IUPAC name for CH3CH2OH?
Ethanol
How do you name an alcohol with more than one -OH group?
By adding prefixes di-, tri-, tetra-, etc.
Which of the following is an industrial use of methanol?
In the production of methanal
Which alcohol has the structure (CH3)3CCH2OH?
2,2-Dimethyl-1-propanol
What happens to the solubility of alcohols in water as the number of carbon atoms increases?
Solubility decreases
Which part of an alcohol is considered hydrophobic?
Alkyl group
Up to how many carbon atoms do alcohols maintain water solubility similar to alkanes?
Nine
How does the boiling point of alcohols change as the number of carbon atoms increases?
Boiling point increases
Which of the following is the most soluble in water?
CH3OH
What type of derivative are alcohols considered?
Organic derivatives of water
What is another term for the hydrophilic part of an alcohol?
Water-loving part
Which of the following influences the boiling point of alcohols?
Intermolecular forces
What is the product formed when ethanoic acid reacts with ethanol?
Ethyl ethanoate
Which catalyst is often used in the esterification process of ethanoic acid with ethanol?
H2SO4
What type of compound is produced when alcohols react with hydrogen halides?
Haloalkanes
What does the hydroxyl group in an alcohol get replaced by in the reaction with a hydrogen halide?
A halogen atom
Which reagent can replace the hydroxyl group in alcohols to form bromoalkanes?
PBr3
Which is a by-product when ethanoic acid reacts with ethanol in an esterification reaction?
Water
Which oxidizing agent can stop the oxidation of primary alcohols at the aldehyde stage?
Pyridinium chlorochromate (PCC)
What is a phenol?
A compound containing a hydroxyl group bonded directly to a benzene ring
Which product is formed when PCC oxidizes 1-Heptanol?
Heptanal
Which of the following oxidizing agents can oxidize secondary alcohols to ketones?
All of the listed agents can perform this oxidation
Why is the oxidation of tertiary alcohols not possible?
The carbon atom does not have any attached hydrogen atoms
Which type of functional group is bonded directly to a benzene ring in phenols?
Hydroxyl group
What happens to the polarity of an alcohol as the number of carbon atoms increases?
The polarity decreases.
What ion is formed when an alcohol reacts with sodium amide?
Alkoxide ion
Which metal reacts least vigorously with alcohols?
Lithium
What product is formed alongside alkoxide ions when alcohols react with alkali metals?
Hydrogen
In the esterification reaction, what replaces the hydroxyl group in the alcohol?
Alkoxy group
What catalyst is typically used in the esterification reaction between an alcohol and a carboxylic acid?
Sulfuric acid
What type of reaction occurs when an alcohol reacts with bromine in the presence of red phosphorus?
Substitution reaction
What is the major product when ethanol reacts with sodium metal?
Sodium ethoxide
Which reagent is used to oxidize primary alcohols to aldehydes?
Collin's reagent
Which product is formed when $CH_3(CH_2)_5CH_2OH$ is oxidized using Collin's reagent?
$CH_3(CH_2)_5CHO$
Which of the following is a commonly used oxidizing agent for oxidizing primary and secondary alcohols?
Pyridinium chlorochromate (PCC)
What are phenols commonly used for?
As germicides and deodorizers
Which product is formed when $CH_3(CH_2)_3CH_2OH$ is oxidized using potassium permanganate?
1-Pentanoic acid
Which reagent is used in the reaction to replace the hydroxyl group of the alcohol with a halogen atom, forming a chloroalkane?
Thionyl chloride
Which of the following is a by-product when $PBr_3$ is used to replace the hydroxyl group of an alcohol with a bromine atom?
$H_3PO_3$
When $CH_3(CH_2)_3CHOHCH_3$ is oxidized, what product is formed?
2-Hexanone
Study Notes
Alcohols
- An alcohol is a compound that contains a hydroxyl group (-OH) bonded directly to a sp3 hybrid carbon atom.
- Alcohols can be described as aliphatic hydroxyl compounds.
- Ethanol is a common example of an alcohol, sourced from the natural fermentation of sugars and starch.
Classification of Alcohols
- Primary alcohol: only one alkyl group is attached to the sp3 hybrid carbon atom (e.g. ethanol, CH3CH2OH)
- Secondary alcohol: two alkyl groups are directly attached to the sp3 hybrid carbon atom
- Tertiary alcohol: three alkyl groups are attached to the sp3 hybrid carbon atom
Naming of Alcohols
- Select the longest continuous chain of carbon atoms that contain the -OH group
- Obtain the parent alkane name of the longest continuous chain of carbon atoms
- Replace the terminal -e of the parent alkane name with -ol
- If the compound contains more than one -OH group, use the endings -diol, -triol, etc.
- If the compound contains other functional groups, name them alphabetically
Physical Properties of Alcohols
- The hydroxyl group is polar and can form hydrogen bonds
- The type of alcohol determines its chemical properties
- Solubility: the hydroxyl group helps the alcohol dissolve in water, but the number of carbon atoms affects solubility (increases with decrease in carbon atoms)
- Boiling point: the hydroxyl group forms hydrogen bonds, increasing the boiling point, and higher molecular weight alcohols have a higher boiling point
Reactions of Alcohols
- Reaction with a strong base: forms an alkoxide ion
- Reaction with alkali metals: forms alkoxide ions
- Reaction with carboxylic acids: forms esters (esterification)
- Reaction with bromine: forms alkyl bromide and hydrogen bromide (substitution reaction)
- Reaction with hydrogen halides: forms haloalkanes
- Reaction with phosphorus tribromide: forms bromoalkane
Oxidation of Alcohols
- Primary alcohols can be oxidized to aldehydes or carboxylic acids
- Secondary alcohols can be oxidized to ketones
- Tertiary alcohols cannot be oxidized
- Oxidizing agents: CrO3, Na2Cr2O7, KMnO4, PCC, Collin's reagent
Phenols
- Compounds that contain a hydroxyl group bonded directly to a benzene ring
- Occur widely in nature, particularly in plants
- Used as colouring materials, disinfectants, germicides, and deodorants
Learn about the basics of alcohols, including their structure and classification. Discover the characteristics of ethanol and its natural sources.
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