(a)
Interpretation:
On the basis of
Concept introduction:
(b)
Interpretation:
On the basis of proton NMR, the compounds
Concept introduction:
Carboxylic acid is a class of organic compound contains a
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Organic Chemistry
- но HO но он The pK, of ascorbic acid (vitamin C) is 4.17, showing that it is slightly more acidic than acetic acid (CH3CO0H, pKa 4.74). (a) Show the fou r different conjugate bases that would be formed by deprotonation of the four different OH groups in ascorbic acid. (b) Compare the stabilities of these four conjugate bases, and predict which OH group of ascorbic acid is the most acidic. (c) Compare the most stable conjugate base of ascorbic acid with the conjugate base of acetic acid, and suggest why these two compounds have similar acidities, even though ascorbic acid lacks the carboxylic acid (COOH) group.arrow_forwardAmine A is a liquid at room temperature and pressure. When vaporised, 0.202g of the amine produces 72.0 cm3 of gas at 1.00 × 105Pa and 100 °C. The 13C NMR spectrum of amine A has 3 peaks. Determine the molecular formula of A and suggest a possible structure for amine A.arrow_forwardDetermine which of the following bases is strong enough to deprotonate acetonitrile (CH3CN), so that equilibrium favors the products:(a) NaH; (b) Na2CO3; (c) NaOH; (d) NaNH2; (e) NaHCO3.arrow_forward
- (i) Draw the dissociation reaction for a carboxylic acid in water and define the Ka for this reaction. Write the equation that relates pKa to Ka. (ii) A deprotonated carboxylic acid can be drawn in two resonance forms. Draw the two forms and explain what the term “resonance” means. (iii) Draw an energy profile for the above dissociation reaction and describe how the profiles for a strong and a weak acid would differ.arrow_forwardProvide an explanation without using the pka values : Why is phenol stronger acid than butanoic acid?arrow_forwardUsing pKa Values to Determine Relative Acidity and Basicity Rank the following compounds in order of increasing acidity, and then rank their conjugate bases in order of increasing basicity.arrow_forward
- 3. Based on the pH results obtained in this experiment, complete the following equation for the reaction of an amine with water. NH2 nH₂O H-O-H + OH-arrow_forwardThe C-H bond in acetone, (CH3)C=O, has a pką of 19.2. Draw two resonance structures for its conjugate base. Then, explain why acetone is much more acidic than propane, CH;CH,CH3 (pKa = 50). %3Darrow_forwardUsing the data in Appendix C, determine which of the following bases is strong enough to deprotonate acetonitrile (CH3CN), so that equilibrium favors the products: (a) NaH; (b) Na2CO3; (c) NaOH; (d) NaNH2; (e) NaHCO3.arrow_forward
- Amphetamine is a powerful stimulant of the central nervous system.Draw the products formed (and show the flow of electrons) from the acid-base reaction of amphetamine with (a) HCl and with (b) NaH.arrow_forward(i) Identify the acidic proton(s) for each of the following carbonyl compounds: O O ( CHỊCH, CÁCH, BỊ CHỊCHỊCH, CÁCH, (2) || (3) CHy-O-C-CH,-C-O-CH, (4) CH,-C-CH, (ii) Rank the compounds (in part (i) above) in the order of increasing or decreasing acidity by using the symbol "" in your answer.arrow_forward19-33 Rank the amines in each set in order of increasing basicity. (b) sbims ne (a) NH2 NH2 N. H (c) H (d) NH2 NH2 NH2 H3C H2 (е) NH2 CH,NH, CONH,arrow_forward
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning