IUPAC Nomenclature of Ethers and Their Properties
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Questions and Answers

What is the correct order of steps in naming an ether according to IUPAC rules?

  • Name the two alkyl substituents and then write the suffix (ether) (correct)
  • Name the larger alkyl substituent and then the smaller one, followed by the suffix (ether)
  • Write the suffix (ether) and then name the alkyl substituent with the highest molecular weight
  • Write the suffix (ether) and then name the two alkyl substituents

    • What is the main reason for the lower boiling points of ethers compared to alcohols?

  • The weaker intermolecular forces between ether molecules (correct)
  • The presence of hydrogen bonding in ethers
  • The presence of a carbonyl group in ethers
  • The higher molecular weight of ethers

    • Which of the following ethers is soluble in water?

  • Diethyl ether
  • Tetraethyl ether
  • Dimethyl ether (correct)
  • Triethyl ether

    • What is the general formula for an aldehyde?

    <p>R-CHO</p> Signup and view all the answers

    What is the reason for the fairly unreactive nature of ethers?

    <p>The nonpolar nature of ethers</p> Signup and view all the answers

    What is the effect of electropositive carbonyl carbon on the O—H bond?

    <p>It pulls electrons away from the O—H bond</p> Signup and view all the answers

    What is the pKa value of F3CCOOH?

    <p>0.23</p> Signup and view all the answers

    What is the general formula of an ester?

    <p>R—COO—R*</p> Signup and view all the answers

    How do you name an ester in IUPAC nomenclature?

    <p>Prefix for the alcohol side, suffix for the acid side</p> Signup and view all the answers

    What is the general formula of an amine?

    <p>R—N(R*)2</p> Signup and view all the answers

    What is the effect of Cr(VI) reagents on primary alcohols and aldehydes?

    <p>They oxidize them to form carboxylic acids</p> Signup and view all the answers

    What is the correct order of naming an amine according to IUPAC rules?

    <p>names of all alkyl substituents linked to the N atom followed by the suffix (amine)</p> Signup and view all the answers

    Why do tertiary amines have a lower boiling point compared to primary and secondary amines?

    <p>They cannot form hydrogen bonds</p> Signup and view all the answers

    What is the result of reacting a primary amine with a large excess of NH3?

    <p>Formation of the primary amine</p> Signup and view all the answers

    What is the reason behind the solubility of small amines in water?

    <p>They can accept hydrogen bonds from water</p> Signup and view all the answers

    What is the product of the reaction between a primary amine and an acid halide?

    <p>An amide</p> Signup and view all the answers

    What type of compound is obtained when a secondary ROH is oxidized?

    <p>Ketone</p> Signup and view all the answers

    What is a functional group responsible for in an organic molecule?

    <p>Center of reactivity</p> Signup and view all the answers

    Which type of hydration of alkynes yields aldehydes?

    <p>Anti-Markovnikov hydration</p> Signup and view all the answers

    What is the general formula of carboxylic acids, where R is a hydrogen or hydrocarbon group?

    <p>RCOOH</p> Signup and view all the answers

    What is the general formula of alkyl halides?

    <p>R–X, where R is a hydrocarbon group and X is a halogen</p> Signup and view all the answers

    Which IUPAC rule for carboxylic acids involves determining the longest continuous chain of carbon atoms starting from the carboxyl group?

    <p>Rule 1</p> Signup and view all the answers

    What is the IUPAC rule for determining the parent name of an alkyl halide?

    <p>The longest continuous chain of carbon atoms that includes the halogen</p> Signup and view all the answers

    What is the prefix used for two halogen substituents on a benzene ring in the 1,3- position?

    <p>m-</p> Signup and view all the answers

    What is the reason for the higher boiling points of carboxylic acids compared to alkanes?

    <p>Polarity</p> Signup and view all the answers

    What is the characteristic of the structure of carboxylic acids?

    <p>Planar sp2 hybridized</p> Signup and view all the answers

    What is the general formula of alcohols?

    <p>R–OH, where R is a hydrocarbon group and OH is a hydroxyl group</p> Signup and view all the answers

    What is the correct IUPAC name for the compound 1,2-dichlorobenzene?

    <p>o-dichlorobenzene</p> Signup and view all the answers

    Study Notes

    Ethers

    • IUPAC nomenclature rules:
      • Write names of two substituents alkyl linked to the O atom
      • Write suffix (ether)
      • Example: CH3‒O‒CH2CH3: ethyl methyl ether
    • No hydrogen bonding is possible in R—O—R
    • Boiling points are much lower than alcohols, similar to haloalkanes
    • Water solubility is much less than alcohols
    • MeOMe and EtOEt have some water solubility, but larger ethers are insoluble, similar to alkanes
    • Fairly unreactive, nonpolar solvents for organic reactions

    Aldehydes

    • Organic compounds containing a carbonyl group (C=O) and at least one hydrogen atom bonded to the carbon in the carbonyl group
    • General formula: RCHO, where R is a hydrocarbon (aliphatic or aromatic) group
    • Electropositive carbonyl carbon pulls electrons away from O—H bond
    • Resulting carboxylate anion is stabilized by resonance
    • Electron withdrawing substituents increase acidity
    • Carboxylate anion is named as an alkanoate (e.g., formate, acetate, pentanoate)

    Synthesis of Carboxylic Acids

    • Oxidation of primary alcohols and aldehydes by Cr(VI) reagents
    • Reaction of carboxylic acid: ester formation

    Esters

    • Organic compounds derived from carboxylic acid and alcohol
    • General formula: RCOOR*, where R is a hydrogen or hydrocarbon (aliphatic or aromatic) group, and R* is a hydrocarbon group
    • IUPAC nomenclature rules:
      • Write suitable prefix for #C, then suffix (….yl) for the side derived from alcohol
      • Write suitable prefix for #C, then suffix (….anoate) for the side derived from carboxylic acid
      • Example: Methyl methanoate, Ethyl butanoate

    Amines

    • Organic compounds containing the C–N linkage
    • General formula: RNH2, R2NH, or R3N, where R is a hydrocarbon group, R* and R** are a hydrogen or hydrocarbon (aliphatic or aromatic) group
    • IUPAC nomenclature rules:
      • Write names of all substituents alkyl linked to the N atom
      • Write suffix (amine)
      • Example: Ethyl amine, Dimethyl amine, Methyl propyl amine, Trimethyl amine
    • Physical properties:
      • N—H less polar than O—H
      • Amines have lower boiling points than alcohols due to weaker hydrogen bonds
      • Tertiary amines have lower boiling points than primary and secondary amines
      • Small amines are soluble in water, branching increases solubility
      • Most amines smell like rotting fish

    Ketones

    • Boiling points are higher than alkanes due to polarity
    • Small carbonyl compounds (< 7 C) are water soluble due to polarity (e.g., acetone)

    Oxidation of Alcohols

    • Secondary ROH gives ketones
    • Primary ROH gives aldehydes

    Ozonolysis of Alkenes

    • Yields ketones or aldehydes

    Hydration of Alkynes

    • Markovnikov hydration yields ketones
    • Anti-Markovnikov hydration yields aldehydes

    Carboxylic Acids

    • Organic compounds containing the carboxyl group (–COOH)
    • General formula: RCOOH, where R is a hydrogen or hydrocarbon (aliphatic or aromatic) group
    • IUPAC nomenclature rules:
      • Determine longest continuous chain of carbon atoms starting from carboxyl group (–COOH) (parent name)
      • Put number for C atoms in the continuous chain of carbon starting from carboxyl group (–COOH)
      • Put numbers and names of substituents alkyl
      • Write suitable prefix for #C, then suffix (….anoic acid)
      • Example: Methanoic acid, Ethanoic acid (formic acid, acetic acid)
    • Planar sp2 hybridized structure
    • Hydrogen bonded dimers
    • Acid-base characteristics

    Aromatic Compounds

    • Functional group: a group of atoms responsible for the chemical behavior of the parent molecule
    • Reactions of benzene: halogen substitution, nitro substitution

    Alkyl Halides

    • Organic compounds containing at least one carbon‒halogen (Cl, Br, I) bond
    • General formula: R–X, where R is a hydrocarbon (aliphatic or aromatic) group, X is Cl, Br, or I
    • IUPAC nomenclature rules:
      • Determine longest continuous chain of carbon atoms in that pass with carbon which links up with halogen (parent name)
      • Put number for C atoms in the continuous chain of carbon starting from terminal C which near to carbon‒halogen bond C‒X
      • Put numbers and names of substituents alkyl
      • Put number carbon which links up with halogen
      • Put numbers and names of halogen as halo (chloro, bromo, iodo), if two halogen or more halogen use (di-, tri-, or tetra- ,…)
      • Write suitable prefix for #C, then suffix (….ane)
      • Example: Flouroethane, 1-iodopropane, 2-bromobutane, 2-bromo-3-methylpentane, 2,3-dichloropentane, 2,4-dibromopentane
    • For two halogen substituents on benzene ring:
      • Use prefixes o- (ortho-), m- (meta-), or p- (para-)

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    Description

    Learn about the rules of naming ethers according to IUPAC, including the correct order of substituents and suffixes. This quiz also covers the physical properties of ethers, such as their boiling points, water solubility, and hydrogen bonding characteristics.

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