16. When cis-1,2-cyclopentanediol reacts with acetone in dry HCl, compound M is formed. What do you expect the hydrolysis of compound M to be when subjected (i) to base; and, (ii) acid a. resistant to base; resistant to acid b. resistant to base; readily hydrolyzed by acid c. readily hydrolyzed by base; resistant to acid d. readily hydrolyzed by base; readily hydorlyzed by acid 17. Following (16), would you expect that a similar compound be formed if the reactant was trans-1,2-cyclopentanediol? Why is this so? a. Yes; hydroxyl groups are on opposite side b. No; hydroxyl groups are on opposite site c. Yes; hydroxyl groups are on the same side d. No; hydroxyl groups are on the same side
16. When cis-1,2-cyclopentanediol reacts with acetone in dry HCl, compound M is formed. What do you expect the hydrolysis of compound M to be when subjected (i) to base; and, (ii) acid a. resistant to base; resistant to acid b. resistant to base; readily hydrolyzed by acid c. readily hydrolyzed by base; resistant to acid d. readily hydrolyzed by base; readily hydorlyzed by acid 17. Following (16), would you expect that a similar compound be formed if the reactant was trans-1,2-cyclopentanediol? Why is this so? a. Yes; hydroxyl groups are on opposite side b. No; hydroxyl groups are on opposite site c. Yes; hydroxyl groups are on the same side d. No; hydroxyl groups are on the same side
Chapter22: Carbonyl Alpha-substitution Reactions
Section22.SE: Something Extra
Problem 18VC
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16. When cis-1,2-cyclopentanediol reacts with acetone in dry HCl, compound M is formed. What do you expect the hydrolysis of compound M to be when subjected (i) to base; and, (ii) acid
a. resistant to base; resistant to acid
b. resistant to base; readily hydrolyzed by acid
c. readily hydrolyzed by base; resistant to acid
d. readily hydrolyzed by base; readily hydorlyzed by acid
17. Following (16), would you expect that a similar compound be formed if the reactant was trans-1,2-cyclopentanediol? Why is this so?
a. Yes; hydroxyl groups are on opposite side
b. No; hydroxyl groups are on opposite site
c. Yes; hydroxyl groups are on the same side
d. No; hydroxyl groups are on the same side
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