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Supply the curved arrows necessary for the following reactions:

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Supply the curved arrows necessary for the following reactions:

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Whereas H3PO4 is a triprotic acid, H3PO3 is a diprotic acid. Draw structures for these two acids that account for this difference in behavior.

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Arrange the following in order of increasing basicity:

(c) CH3CH=CH-, CH3CH2CH2-, CH3≡C-

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Arrange the following in order of increasing basicity:

(b) CH3O-, CH3NH-, CH3CH2-

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Arrange the following in order of increasing basicity:

(a) CH3NH2, CH3NH3+, CH3NH-

 

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Arrange the following compounds in order of decreasing acidity:

 

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Arrange the following compounds in order of decreasing acidity:

(b) CH3CH2CH2OH, CH3CH2CO2H, CH3CHClCO2H

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Arrange the following compounds in order of decreasing acidity:

(a) CH3CH=CH2, CH3CH2CH3, CH3C≡CH

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(b) Arrange the conjugate bases of the acids given in part

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(a) Arrange the following compounds in order of decreasing acidity and explain your answer: CH3CH2NH2, CH3CH2OH, and CH3CH2CH3.

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Starting with appropriate unlabeled organic compounds, show syntheses of each of the following:

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Starting with appropriate unlabeled organic compounds, show syntheses of each of the following:

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Acid HA has pKa = 20; acid HB has pKa = 10.

(a) Which is the stronger acid?

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(a) The Ka of formic acid (HCO2H) is 1.77x 10-4. What is the pKa?

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What reaction will take place if ethyl alcohol is added to a solution of HC≡C:-Na+ in liquid ammonia?

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Write an equation, using the curved-arrow notation, for the acid–base reaction that will take place when each of the following are mixed. If no appreciable acid–base reaction takes place, because the equilibrium is unfavorable, you should so indicate.

(e) CH3CH2Li in hexane and ethyl alcohol

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Write an equation, using the curved-arrow notation, for the acid–base reaction that will take place when each of the following are mixed. If no appreciable acid–base reaction takes place, because the equilibrium is unfavorable, you should so indicate

(d) CH3CH2Li in hexane and ethyne

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Write an equation, using the curved-arrow notation, for the acid–base reaction that will take place when each of the following are mixed. If no appreciable acid–base reaction takes place, because the equilibrium is unfavorable, you should so indicate.

(c) CH3CH2ONa in ethyl alcohol and ethyne

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Write an equation, using the curved-arrow notation, for the acid–base reaction that will take place when each of the following are mixed. If no appreciable acid–base reaction takes place, because the equilibrium is unfavorable, you should so indicate.

(b) Aqueous NaOH and C6H5SO3H

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Write an equation, using the curved-arrow notation, for the acid–base reaction that will take place when each of the following are mixed. If no appreciable acid–base reaction takes place, because the equilibrium is unfavorable, you should so indicate.

(a) Aqueous NaOH and CH3CH2CO2H

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Follow the curved arrows and write the products.

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Follow the curved arrows and write the products.

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Follow the curved arrows and write the products.

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Follow the curved arrows and write the products.

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