Chapter 4: Problem 40
What is the strongest base that can exist in liquid ammonia as a solvent?
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Write equations for the reaction of each compound with $\mathrm{H}_{2} \mathrm{SO}_{4}$, strong protic acid. (a) \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{SCH}_{2} \mathrm{CH}_{3}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NHCH}_{2} \mathrm{CH}_{3}\) (d) \(\mathrm{CH}_{3} \mathrm{NCH}_{3}\) (e) \(\mathrm{CH}_{3}{ }_{\mathrm{C} C H}^{3}\)
Write an equation for the reaction between each Lewis acid-base pair, showing electron flow by means of curved arrows. (a) \(\left(\mathrm{CH}_{3} \mathrm{CH}_{2}\right)_{3} \mathrm{~B}+\mathrm{OH}^{-} \longrightarrow\) (b) \(\mathrm{CH}_{3} \mathrm{Cl}+\mathrm{AlCl}_{3} \longrightarrow\)
Methyl isocyanate, \(\mathrm{CH}_{3}-\mathrm{N}=\mathrm{C}=\mathrm{O}\), is used in the industrial synthesis of a type of pesticide and herbicide known as a carbamate. As a historical note, an industrial accident in Bhopal, India, in 1984 resulted in leakage of an unknown quantity of this chemical into the air. An estimated 200,000 people were exposed to its vapors, and over 2000 of these people died. (a) Write a Lewis structure for methyl isocyanate and predict its bond angles. What is the hybridization of its carbonyl carbon? Of its nitrogen atom? (b) Methyl isocyanate reacts with strong acids, such as sulfuric acid, to form a cation. Will this molecule undergo protonation more readily on its oxygen or nitrogen atom? In considering contributing structures to each hybrid, do not consider structures in which more than one atom has an incomplete octet.
Answer true or false to the following statements about the mechanism of acid- base reactions. (a) The acid and base must encounter each other by a collision in order for the proton to transfer. (b) All collisions between acids and bases result in proton transfer. (c) During an acid-base reaction the lone pair on the base fills the A-H antibonding sigma orbital.
Complete the equation for the reaction between each Lewis acid-base pair. In each equation, label which starting material is the Lewis acid and which is the Lewis base; use curved arrows to show the flow of electrons in each reaction. In doing this problem, it is essential that you show valence electrons for all atoms participating in each reaction. a. b. c. d.
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