a) b) Provide arrows to show the mechanisms and then predict the products of the following acid base reaction. Use pKas to determine which way the reaction will favor (Hint: the lower pka acid will want to dissociate) Дон OH Ha OH NH2 c) H H-O-H
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- (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.Write equations for the following acid-base reactions. Label the conjugate acids and bases, and show any inductive stabilization. Predict whether the equilibrium favors the reactants or products. Try to do this without using a table of pKa values, (a) CH3CH2OH + CH3NH- (b) F3CCOONa + Br3C¬COOH(c) CH3OH + H2SO4 (d) NaOH + H2S(e) CH3NH3+ + CH3O- (f) BrCH2CH2OH + F3C¬CH2O-(g) NaOCH2CH3 + Cl2CHCH2OH (h) H2Se + NaNH2(i) CH3CHFCOOH + FCH2CH2COO- (j) CF3CH2O- + FCH2CH2OHWhich of the following has the lowest pKa value? Hint: a methyl group is an electron donating group which can destabilize the negative charge of the conjugate base. I II III IV
- Rank the following molecules according their acidity. (1 = lowest pka) OEt O 요 ii iiNet il 요 NEt₂ O O CF 3 Predict how the highest pka from question 9 compares with the lowest pka from question 8.Using 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.a) Identify the acidic proton for each of the following molecules: HO OH SH H t t NH₂ b) Rank the compounds in order of increasing acidity using pka values. c) In each case, draw the structure of the conjugate base.
- 2) For each of the following reactions below, predict the products and draw full Lewis structures for the products and reactants. Use curved arrows to show how the proton is transferred in each reaction. Use the table of pKa's given below to determine the position of the equilibrium (to the right or to the left). Acid a) C6H5OH + NaOCH3 pKa 0.18 CF3CO2H CH3CO2H 4.75 b) CH3CO2H + CF3CO2- НCN 9.31 c) HCEC?+ NH3 NH4* 9.25 C6H50H 10.0 CH3OH HCECH 15 25 NH3 39a.) Rank the attached compounds in order of increasing acidity. (b)Which compound forms the strongest conjugate base?The 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). %3D
- As we will see in later chapters, many steps in key reaction sequencesinvolve acid–base reactions. (a) Draw curved arrows to illustrate the flow of electrons in steps [1]–[3]. (b) Identify the base and its conjugate acid in step [1]. (c) Identify the acid and its conjugate base in step [3].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.In the following acid-base reaction, which is the acid, which is the base, which is the conjugate acid and which is the conjugate base: (C2H)- + C3H6O = C2H2 + (C3H6O)-