Questions and Answers
What is the functional group of an alkene?
carbon-to-carbon double bond
What is the functional group of an alkyne?
carbon-to-carbon triple bond
Does CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3 have a functional group?
False
Give the IUPAC name for the compound HOCH2CH2CH2CH2CH2OH.
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Draw the structure for 2-hexanol.
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Draw the structure for 3-methyl-2-pentanol.
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Is isobutyl alcohol primary, secondary, or tertiary?
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What is the LCC in 2-ethyl-1-hexanol?
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Why is ethanol more soluble in water than 1-hexanol?
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Why does 1-butanol have a lower boiling point than 1-hexanol?
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Write the equation for the reaction of 2-butene with water to form 2-butanol.
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Why is methanol more toxic than ethanol?
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How does rubbing alcohol cool a feverish patient?
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Write an equation for the oxidation of CH3CH2CH2CH2CH2OH.
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In a reaction, compound W with the molecular formula C4H10O is converted to compound X with the formula C4H8O. Is W oxidized, reduced, dehydrated, or none of these?
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In a reaction, 2 mol of compound Y with the molecular formula C4H10O is converted to 1 mol of compound Z with the formula C8H18O. Is Y oxidized, reduced, or neither?
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In the oxidation of propylene glycol to pyruvic acid, what functional groups in the reactant are involved?
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How do phenols differ from alcohols in terms of structure and properties?
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How do phenols differ in properties from aromatic hydrocarbons?
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What is the common name for each ether CH3CH2CH2OCH2CH2CH3?
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What is the common name for the ether with the common name derived from isopropyl and methyl groups?
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Why does diethyl ether have a much lower boiling point than 1-butanol?
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Which is more soluble in water—ethyl methyl ether or 1-butanol? Explain.
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Classify each compound as an aldehyde or a ketone.
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Give the IUPAC name for glyceraldehyde, (HOCH2CHOHCHO).
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What feature of their structure makes aldehydes easier to oxidize than ketones?
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How does the carbon-to-oxygen bond of aldehydes and ketones differ from the carbon-to-carbon bond of alkenes?
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What is the functional group of a thiol?
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Write the condensed structural formula for ethanethiol (ethyl mercaptan).
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What is the functional group of a disulfide?
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Write the condensed structural formula for dipropyl disulfide.
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Study Notes
Functional Groups
- Alkenes feature a carbon-to-carbon double bond; alkynes possess a carbon-to-carbon triple bond.
- A compound consisting solely of carbon and hydrogen with all single bonds has no functional group.
IUPAC Naming
- IUPAC naming involves identifying the longest carbon chain and substituents.
- For the compound HOCH2CH2CH2CH2CH2OH, it contains two hydroxyl (OH) groups.
Structural Drawings
- Structures for 2-hexanol and 3-methyl-2-pentanol require the correct placement of OH groups and carbon chain arrangements.
Alcohol Classification
- Isobutyl alcohol is a primary alcohol as the OH-bearing carbon attaches to one other carbon.
- In 2-ethyl-1-hexanol, the longest carbon chain (LCC) is determined by the chain containing the hydroxyl group, totaling seven carbon atoms.
Solubility and Boiling Points
- Ethanol is more soluble in water than 1-hexanol due to its fewer carbon atoms and greater interaction with water.
- 1-hexanol has a higher boiling point than 1-butanol due to its greater molar mass.
Chemical Reactions
- The reaction of 2-butene with water, using sulfuric acid as a catalyst, produces 2-butanol.
- Methanol is more toxic than ethanol as it oxidizes to formaldehyde, a harmful substance.
Cooling Mechanism
- Rubbing alcohol cools the body through heat removal via evaporation.
Oxidation Reactions
- The oxidation of compounds often involves the removal of hydrogen, as seen with compound W to compound X.
- Water removal signifies dehydration rather than oxidation in certain reactions.
Transformation and Functional Groups
- Propylene glycol oxidation introduces ketone and carboxylic acid groups in the product.
- Oxalate ions form via the oxidation of ethylene glycol, typically through precipitation reactions.
Differences Between Compounds
- Phenols differ from alcohols by having an OH group directly attached to an aromatic ring and exhibit weak acidity.
- Compared to aromatic hydrocarbons, phenols are more water-soluble due to the presence of the hydroxyl group.
Ether Naming
- Diethyl ether is named based on the propyl groups surrounding the oxygen atom.
- Isopropyl methyl ether comprises an isopropyl group attached to a methyl group via an ether bond.
Boiling Points in Ethers vs. Alcohols
- Diethyl ether has a lower boiling point than 1-butanol due to the absence of hydrogen bonding.
Aldehydes and Ketones
- Compounds are classified as aldehydes or ketones based on the position of the carbonyl group.
- Aldehydes have the carbonyl group on the terminal carbon, while ketones have it on an internal carbon.
IUPAC Naming Guidelines
- IUPAC naming considers the longest chain and substituents, influencing the final name based on carbon count and positions.
Carbonyl Bonds
- Aldehydes are more easily oxidized than ketones due to the hydrogen atom attached to the carbonyl carbon.
- Carbon-to-oxygen bonds in carbonyl compounds are polar compared to nonpolar carbon-to-carbon bonds in alkenes.
Thiols and Disulfides
- Thiols feature the -SH functional group, with ethanethiol's condensed formula as CH3CH2SH.
- Disulfides contain the -S-S- bond; dipropyl disulfide is represented as CH3CH2CH2SSCH2CH2CH3.
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Description
Test your understanding of functional groups and IUPAC naming from Chemistry Chapter 14. These flashcards cover essential concepts including alkene and alkyne functionalities and evaluation of molecular structures. Perfect for quick revision before exams!
