Concept explainers
(a)
Interpretation:
Products of each possible proton transfer reaction are to be written.
Concept introduction:
A proton transfer reaction is the one in which a Bronsted Lowry base reacts with a Bronsted Lowry acid. A Bronsted Lowry base is a proton acceptor while a Bronsted Lowry acid is a proton donor. The proton is transferred from the acid to the base. The formal charge of the base increases by 1 and that for the acid decreases by 1. The conjugate acid is the species that the base becomes after picking up a proton, and the conjugate base is the species that the acid becomes after losing a proton. A proton transfer reaction is a concerted reaction – that is single step.
(b)
Interpretation:
Among the two possible proton transfer reactions, the reaction that is more energetically favorable is to be determined.
Concept introduction:
Proton transfer reactions favor the side opposite the stronger acid (i.e., opposite the lower pKa). When comparing two uncharged acids, the stronger acid is the one whose negatively charged conjugate base is more stable. If the conjugate base formed is more stable, then the acid will be stronger. An anion becomes more stable as the electronegativity of the atom bearing the negative charge increases. When comparing two positively charged acids, the stronger acid is the one that is less stable.
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Organic Chemistry: Principles and Mechanisms (Second Edition)
- Explain why the bond dissociation energy for bond (a) is lower than the bond dissociation energy for bond (b).arrow_forwardBy using only electron density arguments, determine whether the following reactions will occur.arrow_forwardGiven the curved arrow notation for each of the following proton transfer reactions, draw the appropriate products. (a) (b) ? OH: (c) (d) H- ? ? :0arrow_forward
- Follow the format of solving the problem where you should write the GIVEN, ASKED, SOLUTION, and ANSWER. Add curved arrows to the following reactions to indicate the flow of electrons for all of the bond-forming and bond-breaking steps.arrow_forward3. (a) Draw the appropriate curved arrows and products for each set of reactants undergoing a coordination step. Identify each reactant species as either a Lewis acid or a Lewis base. (b) Use curved arrow notation to show each product undergoing heterolysis to regenerate reactants. (0) (ii) NH₂ H₂O + BF3 + AICI3arrow_forwardRank the molecules in decreasing (strongest to weakest) acidity. Include ALL resonance structures with arrows and explain reasoning for rank.arrow_forward
- (b) Addition of HBr to the alkene in the presence of peroxide form radical intermediates. Based on the following reaction, use the curved arrows to HBr B (preferred product) ROOR (i) show the initiation step of this reaction. (ii) draw the possible structures of the two radicals formed in the propagation step. (ii) explain the formation of the preferred product B.arrow_forwardwhich is most basic among the three?arrow_forwardWhich of the following two reactions would you predict to go faster and why?.arrow_forward
- What would the conjugate acid of (CH3C≡ C:–) look like in bond-line structure?arrow_forwardDraw the curved arrows and the product for each of the following nucleophilic addition steps. (a) (b) + CH,OK ? + CH3LI (c) MgBr (d) ? + NABH4 ? (e) (f) O → ? ? + N2OH +arrow_forwardThe carbocation shown here is formed in one step of an electrophilic aromatic substitution reaction (discussed in Chapter 22). (a) Draw the curved arrow notation and the product for the elimination of H*. (b) Do the same for the elimination of SO3H*. НО O: S: O= H,0 ?arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning