40 Questions
What is the primary reason for the solubility of alcohols in water?
Hydrogen Bonding between alcohol and water molecules
What is the IUPAC rule for naming alcohols with multiple bonds, halogens, and alkyl groups?
Alcohol has priority over multiple bonds, halogens, and alkyl groups
What is the IUPAC name of the alcohol CH3CH2CH2CH2CHCH2OH?
2-propyl-1-hexanol
What is the IUPAC name of the cyclic alcohol CH3OH?
Cyclohexanol
What is the medically important alcohol with the formula CH3CH2OH?
Ethanol (Ethyl alcohol)
What is the general formula for alcohols?
R-OH
What is the correct IUPAC name for the following compound?
3-ethyl-5-methylcyclohexanol
Why do alcohols have higher boiling points compared to hydrocarbons of comparable molecular weight?
Due to their ability to form hydrogen bonds
Which of the following is an example of a medically important alcohol?
All of the above
What is the common name for the following compound?
benzyl alcohol
What is the correct IUPAC name for the compound with the following structural formula?
3-penten-2-ol
What is the IUPAC name for the compound CH₃CH₂CH₂OH?
Butanol
What is the correct naming of the hydroxyl group when it occurs in the same molecule with carboxylic acid, aldehyde, or ketone functionalities?
It is named as a substituent
What is the reaction that involves the hydration of alkenes to form alcohols?
Hydration of alkenes
What is the common name for the compound with the following structural formula?
cyclohexanol
What is the primary use of methanol?
As a solvent
Which of the following alcohols is commonly used as a disinfectant and has a slight odor?
2-Propanol (Isopropyl alcohol)
What is the reaction that produces an alkene from an alcohol?
Dehydration
What is the primary function of 1,2-Ethanediol (Ethylene glycol) in automobiles?
As an antifreeze
What is the functional group of an alcohol?
-OH
What is the major product of the dehydration reaction of 3-methyl-2-butanol?
The alkene with the greatest number of alkyl groups on the double bonded carbon
What type of alcohols can undergo dehydrogenation to form aldehydes and ketones?
Only primary and secondary alcohols
What is the role of a strong acid in the dehydration of alcohols?
To catalyze the formation of the alkene
What is the general trend in the dehydration of alcohols?
The alkene with the greatest number of alkyl groups on the double bonded carbon is always the major product
What is the result of heating an alcohol with a strong acid?
The formation of an alkene and water
Why do phenols react more easily with sodium hydroxide than alcohols?
Phenols have a stronger resonance stabilization than alcohols
What is the reason why alcohols do not react with sodium hydroxide to form alkoxides?
Alkoxides are stronger bases than hydroxide
What type of base can react with aliphatic alcohols to form alkoxide ions?
Sodium hydride
What is the product of the reaction between t-butyl alcohol and potassium metal?
Potassium t-butoxide
What is the reaction between p-nitrophenol and aqueous potassium hydroxide?
A neutralization reaction occurs
Why do phenols have increased acidity relative to aliphatic alcohols?
Due to stronger resonance stabilization
What is the reaction between cyclohexanol and aqueous potassium hydroxide?
No reaction occurs
What is the role of sodium hydride in the reaction with aliphatic alcohols?
It acts as a base
What is the product of the reaction between an aliphatic alcohol and sodium hydride?
Sodium alkoxide
Why do phenols react more easily with sodium hydroxide than aliphatic alcohols?
Phenols have a stronger resonance stabilization than aliphatic alcohols
What is the oxidation product of a primary alcohol oxidized by PCC?
Aldehyde
What is not a characteristic of phenols?
Strong oxidizing agent
What is the product of oxidizing a tertiary alcohol?
No reaction
What is the reagent used to oxidize a primary alcohol to an aldehyde?
Pyridinium chlorochromate (PCC)
What is the definition of oxidation in organic systems?
Gain of oxygen and loss of hydrogen
Study Notes
Dehydration of Alcohols to Alkenes
- Alcohols can be dehydrated by heating them with a strong acid to produce alkenes.
- The reaction is an elimination reaction, where the -OH and -H are removed from adjacent carbon atoms to form an alkene and water.
Zaitsev's Rule
- Zaitsev's rule states that in an elimination reaction, the alkene with the greatest number of alkyl groups on the double bonded carbon is the major product of the reaction.
- The rule is used to predict the major and minor products of dehydration reactions.
Oxidation of Alcohols
- Primary alcohols can be oxidized to carboxylic acids using strong oxidizing agents such as CrO3 or H2CrO4.
- Secondary alcohols can be oxidized to ketones using mild oxidizing agents such as PCC (pyridinium chlorochromate).
- Tertiary alcohols do not undergo oxidation reactions.
Physical Properties of Alcohols
- Hydrogen bonding between alcohol molecules and between alcohol and water molecules is responsible for the high boiling points and solubility of alcohols in water.
- As the molecular weight of an alcohol increases, its boiling point increases, but its solubility in water decreases.
IUPAC Nomenclature of Alcohols
- The IUPAC name of an alcohol is based on the longest chain containing the OH carbon.
- The -e of the alkane name is replaced with -ol.
- The chain is numbered from the end giving the -OH carbon the lower number.
- The name is prefixed with the number indicating the position of the OH group.
Medically Important Alcohols
- Methanol: used as a solvent, toxic if ingested, and can cause blindness and death.
- Ethanol: used as a solvent, in alcoholic beverages, and as a fuel.
- 2-Propanol (isopropyl alcohol): used as a disinfectant, astringent, and industrial solvent.
- 1,2-Ethanediol (ethylene glycol): used as an automobile antifreeze, has a sweet taste, but is extremely poisonous.
Preparation of Alcohols
- Alcohols can be prepared by hydration of alkenes or hydrogenation of aldehydes and ketones.
- The reaction requires a catalyst such as acid or Pt, Pd, or Ni.
Phenols
- Phenols are compounds in which the hydroxyl group is attached to a benzene ring.
- Phenols are polar compounds due to the hydroxyl group.
- Phenols have the formula Ar-OH, where Ar is an aromatic ring.
- Phenols have different properties compared to aliphatic alcohols due to the aromaticity of the ring.
Test your knowledge of alcohols, including their solubility in water, boiling points, and naming conventions according to IUPAC rules. Learn about the effects of hydrogen bonding on their physical properties.
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