Concept explainers
Interpretation:
Phenol is considerably stronger acid than cyclohexanol; the reason has to be proposed.
Concept Introduction:
Base and its conjugate Acid: A Base is a species that can gain a proton. When a base gains a proton
Electron delocalization stabilizes base: If a base has delocalized electrons, then the negative charge that results when the base’s conjugate acid loses a proton will belong to one atom. If a base has delocalized electrons, then the negative charge that results when the base’s conjugate acid loses a proton will be shared by two or more atoms. A base with delocalized electron is more stable than a similar base with localized electrons.
Effect of hybridization on Acidity: The electronegativity of an atom depends on its hybridization.
The stronger acid will have its proton attached to the more electronegative atom.
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Chapter 10 Solutions
Organic Chemistry
- Draw the structure of a compound fitting each description: a.an aldehyde with molecular formula C4H8O b. ketone with molecular formulab C4H8O c. a carboxylic acid with molecular formula C4H8O2 d. an ester with molecular formula C4H8O2arrow_forwardArrange the following compounds in the increasing order of their acid strength: p-cresol, p-nitrophenol, phenolarrow_forwardArrange these compounds in order of increasing acidity: 2,4-dichlorophenol, phenol, cyclohexanol.arrow_forward
- The following molecule belongs to a class of compounds called enediols; each carbon of the double bond carries an OH group. Draw structural formulas for the -hydroxyketone and the -hydroxyaldehyde with which this enediol is in equilibrium.arrow_forwardFollowing is the structural formula of the tranquilizer meparfynol (Oblivon). Propose a synthesis for this compound starting with acetylene and a ketone. (Notice the -yn- and -ol in the chemical name of this compound, indicating that it contains alkyne and hydroxyl functional groups.)arrow_forwardComplete each acid-base reaction and predict whether the position of equilibrium lies toward the left or toward the right. (a) CH3CCH+CH3CH2ONa+CH3CH3OH (b) CH3CCCH2CH2OH+Na+NH2NH3(l)arrow_forward
- Aldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in which there is one hydroxyl group and one ether-like group. Reaction of a hemiacetal with a second molecule of alcohol gives an acetal and a molecule of water. We study this reaction in Chapter 16. Draw structural formulas for the hemiacetal and acetal formed from these reagents. The stoichiometry of each reaction is given in the problem.arrow_forwardUsing your reaction roadmaps as a guide, show how to convert propane into propyl propanoate. You must use propane as the source of all carbon atoms in the target molecule. Show all reagents needed and all molecules synthesized along the way.arrow_forwardA problem often encountered in the oxidation of primary alcohols to acids is that esters are sometimes produced as by-products. For example, oxidation of ethanol yields acetic acid and ethyl acetate: Propose a mechanism to account for the formation of ethyl acetate. Take into account the reversible reaction between aldehydes and alcohols:arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning