Which of the given solvents will be compatible with the acids and bases involved in the following reactions (Ignoring any side reactions)?

Solvent choices = diethyl ether, ethanol, and water.

a. CH₃CH₂Li + CH₃—C≡C—H → CH₃—CH₃ + CH₃—C≡CLi 

b. CH₃CH₂Li + (CH₃)₂CH—OH → CH₃—CH₃ + (CH₃)₂CH—OLi 

Using the given K_eq value, identify the weakest acid and the weakest base in the reaction given below.

Which of the compounds given below can be deprotonated by CH₃O⁻ in an acid-base reaction that favors product formation? (pK_a of CH₃OH = 15.9)
(i) HCOOH (pK_a = 3.7)
(ii) CH₃NH₂ (pK_a = 40)
(iii) NH₄⁺ (pK_a = 9.4)
(iv) HC≡CH (pK_a = 25)

Ethoxide cannot be used to deprotonate cyclohexane in a reaction that favors the formation of a carbanion. Explain why this is true.

An acid-base equilibrium favors the formation of the weaker acid. Which of the following reactions favor the formation of products?

Some equations of acid-base reactions are given below. Write the products in each case if any significant reaction is possible.

a. CH₃—C≡C—H + NaOH
b. CH₃—C≡C—H + CH₃Li
c. CH₃—C≡C—H + NaNH₂

For the acid-base reactions below, prove that the equilibrium lies in the direction indicated in the reactions by comparing the pK_a values of the acids on both sides of the equilibrium arrow.