Untitled Quiz
45 Questions
0 Views

Choose a study mode

Play Quiz
Study Flashcards
Spaced Repetition
Chat to Lesson

Podcast

Play an AI-generated podcast conversation about this lesson

Questions and Answers

What is the structural formula for 1-methylpropyl?

  • - CH(CH3)CH(CH3)
  • - CH(CH3)CH2CH3 (correct)
  • - CCH3
  • - CH2CH2CH3

Which name corresponds to the structural formula - CH3?

  • butyl
  • propyl
  • methyl (correct)
  • ethyl

What is the condensed structural formula for 2-methylpropyl?

  • - CH(CH3)CH2CH3 (correct)
  • - C(CH3)2CH2
  • - CH3CHCH3
  • - CH2(CH3)2

Identify the structural formula for tert-butyl.

<ul> <li>C(CH3)3 (D)</li> </ul> Signup and view all the answers

Which of the following represents the condensed formula for propyl?

<ul> <li>CH2CH2CH3 (C)</li> </ul> Signup and view all the answers

What does Zaitsev’s rule state regarding hydrogen atom loss during intramolecular alcohol dehydration?

<p>Hydrogen loss occurs from the carbon adjacent to the hydroxyl-bearing carbon with the fewest hydrogen atoms. (B)</p> Signup and view all the answers

At what temperature does intermolecular alcohol dehydration typically occur for primary alcohols?

<p>140°C (A)</p> Signup and view all the answers

What is the product of intermolecular alcohol dehydration?

<p>Ether (D)</p> Signup and view all the answers

Which statement is true regarding the behavior of secondary and tertiary alcohols during dehydration?

<p>They always yield alkene products. (D)</p> Signup and view all the answers

What is the preferred alkene product formed from dehydration of 2-butanol?

<p>2-butene (C)</p> Signup and view all the answers

What type of reaction is described in the dehydration of alcohols?

<p>Condensation reaction (B)</p> Signup and view all the answers

Why is Zaitsev's rule particularly useful when predicting product formation in alcohol dehydration?

<p>It helps identify the preferred carbon for hydrogen loss. (C)</p> Signup and view all the answers

Which of the following statements is incorrect regarding the reactions of alcohols?

<p>Primary alcohols usually produce alkenes rather than ethers when dehydrated. (A)</p> Signup and view all the answers

What is the correct suffix added to the name of a hydrocarbon group attached to the oxygen atom in an ether when both groups are identical?

<p>di (A)</p> Signup and view all the answers

Which of the following correctly represents the IUPAC naming convention for ethers?

<p>The base name is derived from the longest carbon chain. (A)</p> Signup and view all the answers

What change is made to the hydrocarbon group's name when it becomes an alkoxy group?

<p>The '-yl' ending is replaced with '-oxy'. (C)</p> Signup and view all the answers

Which ether can exhibit constitutional isomerism?

<p>C4 ether (B), C5 ether (C)</p> Signup and view all the answers

In the case of the ether named '2-Ethoxybutane', what does 'ethoxy' indicate?

<p>It indicates the presence of a two-carbon alkyl group attached to the base chain. (B)</p> Signup and view all the answers

What is a necessary consideration when determining constitutional isomerism in ethers?

<p>The partitioning of carbon atoms between the two alkyl groups. (B)</p> Signup and view all the answers

What is the main characteristic that distinguishes thiols from alcohols and ethers?

<p>Thiols have stronger characteristic odors. (B)</p> Signup and view all the answers

What is the typical state of dimethyl sulfide at room temperature?

<p>Gas (A)</p> Signup and view all the answers

Which of the following correctly names a compound with both ethyl and methyl groups attached to oxygen?

<p>Ethyl methyl ether (C)</p> Signup and view all the answers

What is the minimum number of carbon atoms needed in an ether for constitutional isomerism to be possible?

<p>4 carbon atoms (D)</p> Signup and view all the answers

Which of the following is true about thioethers?

<p>They use sulfide in place of ether in common names. (C)</p> Signup and view all the answers

Which compounds are typically produced by bacteria in the mouth that contribute to 'morning breath'?

<p>Hydrogen sulfide and dimethyl sulfide (A)</p> Signup and view all the answers

What type of bond is weaker than a carbon-oxygen bond?

<p>Carbon-sulfur (B)</p> Signup and view all the answers

What do garlic and onions have in common regarding their sulfur-containing compounds?

<p>Many sulfur-containing compounds formed are common to both garlic and onions. (B)</p> Signup and view all the answers

What is the perception of the smell of fried onions?

<p>Considered pleasant by most people. (D)</p> Signup and view all the answers

How are thiols and thioethers alike in terms of chemical properties?

<p>Both exhibit functional group isomerism. (A)</p> Signup and view all the answers

Which of the following types of isomerism is possible for alcohols with three or more carbon atoms?

<p>Constitutional isomerism (D)</p> Signup and view all the answers

Methanol is commonly referred to as which of the following?

<p>Wood alcohol (B)</p> Signup and view all the answers

What is the main toxic byproduct produced when methanol is oxidized by alcohol dehydrogenase in the body?

<p>Formaldehyde (C)</p> Signup and view all the answers

What substance is used to treat methanol poisoning by inhibiting its oxidation?

<p>Ethanol (B)</p> Signup and view all the answers

Which alcohol is produced from the fermentation of grains such as corn and barley?

<p>Ethyl alcohol (B)</p> Signup and view all the answers

What is the maximum concentration of ethanol that can be produced through yeast fermentation?

<p>18% (A)</p> Signup and view all the answers

Methyl alcohol is primarily produced today through which of the following reactions?

<p>Reaction between H2 and CO (B)</p> Signup and view all the answers

Which statement about ethanol's concentration during fermentation is true?

<p>It maximizes at about 18% due to yeast inactivation. (A)</p> Signup and view all the answers

Why do alcohols have higher boiling points than alkanes of similar molecular mass?

<p>Alcohols can form hydrogen bonds. (A)</p> Signup and view all the answers

How are alcohols primarily prepared from alkenes?

<p>By hydration reactions in the presence of sulfuric acid. (C)</p> Signup and view all the answers

What is the classification of a primary alcohol?

<p>One hydroxyl group and a carbon atom bonded to only one other carbon atom. (D)</p> Signup and view all the answers

What does Markovnikov's rule help to determine?

<p>The predominant alcohol product from alkene reactions. (D)</p> Signup and view all the answers

What feature differentiates tertiary alcohols from other types?

<p>They have a hydroxyl group attached to a carbon bonded to three other carbons. (B)</p> Signup and view all the answers

Which of the following statements about the solubility of alcohols is true?

<p>Alcohols have much higher solubility in water than alkanes of similar molecular mass. (C)</p> Signup and view all the answers

In the process of adding H2 to a carbonyl group, what is the result?

<p>Addition of hydrogen to both the carbon and oxygen atoms. (D)</p> Signup and view all the answers

Which type of alcohol is characterized by the hydroxyl group connected to a carbon bonded to two other carbons?

<p>Secondary alcohol (2o) (C)</p> Signup and view all the answers

Flashcards

Butyl Group

An alkyl group with four carbon atoms in a chain.

Isobutyl Group

An alkyl group with four carbon atoms, branched at the second carbon.

Sec-Butyl Group

An alkyl group with four carbon atoms, branched near the end.

tert-Butyl Group

An alkyl group with four carbon atoms, branched at the first carbon.

Signup and view all the flashcards

Methyl Group

An alkyl group with one carbon atom.

Signup and view all the flashcards

Zaitsev's Rule (Alcohol Dehydration)

In alcohol dehydration to form an alkene, hydrogen loss preferentially occurs from the carbon atom adjacent to the hydroxyl-bearing carbon with fewest hydrogens.

Signup and view all the flashcards

Alcohol Dehydration (Intramolecular)

A chemical reaction where an alcohol molecule loses a water molecule to form an alkene.

Signup and view all the flashcards

Intermolecular Alcohol Dehydration

Two alcohol molecules combine to form an ether, while losing a water molecule. (Condensation reaction)

Signup and view all the flashcards

Primary Alcohol

An alcohol where the carbon atom bearing the hydroxyl group is attached to only one other carbon atom.

Signup and view all the flashcards

Secondary Alcohol

An alcohol where the carbon bearing the hydroxyl group is attached to two other carbon atoms.

Signup and view all the flashcards

Tertiary Alcohol

An alcohol where the carbon bearing the hydroxyl group is attached to three other carbons.

Signup and view all the flashcards

Alkene

An unsaturated hydrocarbon containing a carbon-carbon double bond.

Signup and view all the flashcards

Ether

A compound with a carbon-oxygen-carbon connection (R-O-R).

Signup and view all the flashcards

Naming Ethers (basic rule)

Name the two hydrocarbon groups attached to the oxygen atom, and add the word "ether". List hydrocarbon groups alphabetically.

Signup and view all the flashcards

Naming Ethers (same R group)

When both hydrocarbon groups (R groups) are the same, use the prefix "di" with the R group name, followed by "ether".

Signup and view all the flashcards

IUPAC Nomenclature for Ethers (Rule 1)

Select the longest carbon chain to name the base part of the ether.

Signup and view all the flashcards

IUPAC Nomenclature for Ethers (Rule 2)

Change the "yl" ending of the other hydrocarbon group to "oxy".

Signup and view all the flashcards

IUPAC Nomenclature for Ethers (Rule 3)

Put the alkoxy group name, with a locator number, in front of the base chain name.

Signup and view all the flashcards

Ether Isomerism (condition 1)

Isomerism in ethers depends on how the carbon atoms are divided between the two alkyl groups.

Signup and view all the flashcards

Ether Isomerism (condition 2)

Isomerism possibilities also depend on the isomerism possibilities in the individual alkyl groups.

Signup and view all the flashcards

Ether Isomerism (limitation)

Isomerism is not possible for C2 or C3 ethers but possible for C4 and C5 ethers.

Signup and view all the flashcards

Thioethers

Organic compounds containing a carbon-sulfur-carbon bond, similar to ethers but with sulfur replacing oxygen.

Signup and view all the flashcards

Thiols

Organic compounds containing a sulfur-hydrogen bond (R-SH), analogous to alcohols but with sulfur replacing oxygen.

Signup and view all the flashcards

Carbon-sulfur bond strength

A carbon-sulfur covalent bond is weaker than a carbon-oxygen bond.

Signup and view all the flashcards

Thioether naming

Thioethers are named like ethers, but with "sulfide" instead of "ether" in common names and "alkylthio" for IUPAC.

Signup and view all the flashcards

Dimethyl sulfide

A simple thioether with two methyl groups attached to a sulfur atom (CH3-S-CH3), a gas at room temperature.

Signup and view all the flashcards

Ethyl methyl sulfide

A thioether with an ethyl group and a methyl group attached to sulfur (CH3CH2-S-CH3), a liquid at room temperature.

Signup and view all the flashcards

Functional Group Isomerism

Thiols and thioethers can have the same molecular formula as alcohols and ethers, but different arrangements of atoms, leading to different properties.

Signup and view all the flashcards

Oral Bacteria and Odor

Bacteria in the mouth produce compounds like hydrogen sulfide, methanethiol (a thiol), and dimethyl sulfide (a thioether), contributing to bad breath.

Signup and view all the flashcards

What makes alcohols different from alkanes?

Alcohols have higher boiling points and are more soluble in water compared to alkanes with similar molecular masses.

Signup and view all the flashcards

Hydrogen Bonding in Alcohols

The presence of the hydroxyl group (-OH) in alcohols allows for hydrogen bonding, which is a strong intermolecular force.

Signup and view all the flashcards

Alcohol Hydration

The addition of water to an alkene in the presence of an acid catalyst (H2SO4) produces an alcohol.

Signup and view all the flashcards

Markovnikov's Rule

In the addition of water to an unsymmetrical alkene, the hydrogen atom attaches to the carbon with more hydrogen atoms already present.

Signup and view all the flashcards

Addition of H2 to Carbonyl

Adding H2 to a carbonyl group (C=O) is similar to adding H2 to a double bond, with one H going to carbon and the other to oxygen.

Signup and view all the flashcards

Constitutional Isomers (Alcohols)

Molecules with the same molecular formula but different structural arrangements of atoms, specifically in the case of alcohols with 3 or more carbon atoms.

Signup and view all the flashcards

Skeletal Isomers

Constitutional isomers where the carbon skeleton (backbone) differs in its arrangement.

Signup and view all the flashcards

Positional Isomers

Constitutional isomers where the position of the functional group (hydroxyl group, -OH) differs on the carbon chain.

Signup and view all the flashcards

Methyl Alcohol (Methanol)

The simplest alcohol, used as a fuel and solvent, commonly known as wood alcohol due to its early production method; it is highly toxic to the body, especially the eyes.

Signup and view all the flashcards

Ethanol

Also known as grain alcohol, this alcohol is produced by fermenting grains like corn, rice, and barley. It is a commonly used solvent and fuel.

Signup and view all the flashcards

Maximum Ethanol Concentration by Fermentation

Yeast enzymes responsible for fermentation get deactivated at higher concentrations of ethanol, limiting the maximum concentration achievable to 18%.

Signup and view all the flashcards

Ethanol Treatment for Methanol Poisoning

Ethanol competes with alcohol dehydrogenase, the enzyme responsible for oxidizing methanol into toxic substances, preventing further breakdown of methanol.

Signup and view all the flashcards

Alcohol Dehydrogenase

An enzyme in the human body that oxidizes alcohols. It primarily breaks down ethanol in alcoholic beverages.

Signup and view all the flashcards

Study Notes

General, Organic, and Biological Chemistry - Chapter 14

  • Chapter covers Alcohols, Phenols, and Ethers

Chapter 14 - Table of Contents

  • 14.1 Bonding Characteristics of Oxygen Atoms in Organic Compounds
  • 14.2 Structural Characteristics of Alcohols
  • 14.3 Nomenclature for Alcohols
  • 14.4 Isomerism for Alcohols
  • 14.5 Important Commonly Encountered Alcohols (e.g., Methanol, Ethanol, Isopropyl Alcohol)
  • 14.6 Physical Properties of Alcohols
  • 14.7 Preparation of Alcohols
  • 14.8 Classification of Alcohols (primary, secondary, tertiary)
  • 14.9 Chemical Reactions of Alcohols (combustion, intramolecular dehydration, oxidation, halogenation)
  • 14.10 Polymeric Alcohols
  • 14.11 Structural Characteristics of Phenols
  • 14.12 Nomenclature for Phenols
  • 14.13 Physical and Chemical Properties of Phenols (acidity)
  • 14.14 Occurrence of and Uses for Phenols (antiseptic, antioxidant properties)
  • 14.15 Structural Characteristics of Ethers
  • 14.16 Nomenclature for Ethers
  • 14.17 Isomerism for Ethers
  • 14.18 Physical and Chemical Properties of Ethers (flammability, uses as anesthetics)
  • 14.19 Cyclic Ethers
  • 14.20 Sulfur Analogs of Alcohols (thiols, properties)
  • 14.21 Sulfur Analogs of Ethers (thioethers, properties)

Section 14.1 - Bonding Characteristics of Oxygen Atoms in Organic Compounds

  • Oxygen is a Group VIA element
  • Has 6 valence electrons
  • Has two lone pairs
  • Can form two covalent bonds (two single bonds or one double bond)

Section 14.2 - Structural Characteristics of Alcohols

  • A hydroxyl (-OH) group bonded to a saturated carbon atom constitutes an alcohol
  • General structure: R-OH
  • Examples: CH3OH, C3H7OH

Section 14.3 - Nomenclature for Alcohols (Common Names)

  • For C1-C4 alkyl groups, name all carbon atoms as a single alkyl group (methyl, ethyl, propyl, butyl)
  • Add the word "alcohol"

Section 14.4 - Isomerism for Alcohols

  • Constitutional isomerism is possible for alcohols with 3 or more carbon atoms
  • Two types of isomers: Skeletal and positional isomers

Section 14.5 - Important Commonly Encountered Alcohols

  • Methanol: A good fuel and solvent; formerly produced by heating wood; toxic, can cause blindness.
  • Ethanol: Grain alcohol; prepared from yeast fermentation of plant sugars; excellent solvent and fuel; toxic effects include hangover.
  • Isopropyl Alcohol: Three-carbon alcohol; used as rubbing alcohol; toxic, faster elimination, and may induce vomiting

Section 14.6 - Physical Properties of Alcohols

  • Alcohol molecules exhibit both polar and nonpolar character
  • Boiling points tend to increase with the length of the carbon chain
  • Small monohydroxy alcohols are completely soluble in water
  • Solubility decreases beyond three carbons (longer chains)

Section 14.7 - Preparation of Alcohols

  • Prepared by hydration of alkenes
  • Alkenes react with water in presence of sulfuric acid
  • Markovnikov's rule is used to predict predominant alcohol product

Section 14.8 - Classification of Alcohols

  • Primary alcohol (1°): Hydroxyl group attached to one other carbon atom
  • Secondary alcohol (2°): Hydroxyl group attached to two other carbon atoms
  • Tertiary alcohol (3°): Hydroxyl group attached to three other carbon atoms

Section 14.9 - Chemical Reactions of Alcohols

  • Combustion: Produces carbon dioxide and water
  • Intramolecular Dehydration: Removing water (-H and -OH) from a single molecule to form an alkene (Zaitsev's rule applies to predict the predominant product)
  • Oxidation: Increasing C-O bonds and/or decreasing C-H bonds (primary alcohols yield aldehydes, then carboxylic acids; secondary alcohols yield ketones; tertiary alcohols do not react)
  • Halogenation: Substituting a halogen atom for the hydroxyl group to form an alkyl halide

Section 14.10 - Polymeric Alcohols

  • Synthesis of polymeric alcohols with structures similar to substituted polyethylenes
  • Polyvinyl alcohol (PVA) is a tough, water-soluble polymer with uses in films, tubes, and fibers

Section 14.11 - Structural Characteristics of Phenols

  • Phenol: An -OH group attached to an aromatic ring
  • Aryl group: Aromatic carbon ring system where one hydrogen has been removed
  • General formula for aryl alcohol: Ar-OH

Section 14.12 - Nomenclature for Phenols

  • Name "phenol” and indicate position of substituent with a number followed by the name

Section 14.13 - Physical and Chemical Properties of Phenols

  • Phenols are usually low-melting solids or liquids at room temp
  • Sparingly soluble in water
  • Many phenols have antiseptic and disinfectant properties
  • Phenol itself is a simple phenol, a colorless solid with a medicinal odor with a melting point of 41°C and greater water solubility than other phenols
  • Phenols are weak acids in solution

Section 14.14 - Occurrence of and Uses for Phenols

  • Many phenols (e.g., 4-hexylresorcinol, o-phenylphenol, 2-benzyl-4-chlorophenol) have antiseptic properties
  • Some phenols have antioxidant properties (e.g., BHA, BHT, Vitamin E) & as flavoring agents and/or antibacterials

Section 14.15 - Structural Characteristics of Ethers

  • Ethers: An oxygen atom bonded to two carbon atoms
  • General formula: R—O—R

Section 14.16 - Nomenclature for Ethers

  • Name the two hydrocarbon groups and the word "ether"
  • List the hydrocarbon groups alphabetically
  • Use "di" if both hydrocarbon groups are the same

Section 14.17 - Isomerism for Ethers

  • Ethers with greater than two alkyl groups exhibit constitutional isomerism
  • Isomers: Different arrangements of the atoms in the molecule for the same molecular formula
  • C2 and C3 ethers do not exhibit constitutional isomerism

Section 14.18 - Physical and Chemical Properties of Ethers

  • Boiling points are similar to alkanes of the same molecular mass

Section 14.19 - Cyclic Ethers

  • Cyclic ethers contain the ether functional group as part of a ring system (heterocyclic organic compounds)

Section 14.20 - Sulfur Analogs of Alcohols (Thiols)

  • Thiols (R-SH): Sulfur analogue of alcohols
  • Lower boiling point than corresponding alcohol due to lack of hydrogen bonding
  • Strong unpleasant odor

Section 14.21 - Sulfur Analogs of Ethers (Thioethers)

  • Thioethers (R-S-R): Sulfur analogue of ethers
  • Less reactive than alcohols and ethers.
  • Exhibit functional-group isomerism like alcohols and ethers

Studying That Suits You

Use AI to generate personalized quizzes and flashcards to suit your learning preferences.

Quiz Team

Related Documents

Chapter 14 Alcohols, Phenols, and Ethers PDF

More Like This

Untitled Quiz
6 questions

Untitled Quiz

AdoredHealing avatar
AdoredHealing
Untitled Quiz
37 questions

Untitled Quiz

WellReceivedSquirrel7948 avatar
WellReceivedSquirrel7948
Untitled Quiz
55 questions

Untitled Quiz

StatuesquePrimrose avatar
StatuesquePrimrose
Untitled Quiz
50 questions

Untitled Quiz

JoyousSulfur avatar
JoyousSulfur
Use Quizgecko on...
Browser
Open
Browser
Browser