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Solutions to Problems 29 (d) CH₃⁻ + NH₃ CH₄ + NH₂⁻ stronger base stronger acid weaker acid weaker base (e) + Cl⁻ H₂O + ≈ weaker acid weaker base stronger base stronger acid (f) CH₃COOH + CH₃S⁻ + CH₃SH = 2.0 X 10⁵ stronger acid stronger base weaker base weaker acid H 28. (a) H-O-H H + H + -:CN: H (b) :0: :0: (c) H H (d) H H H-N-H CH₄ + :NH₂ H (e) H + H :0: :0: (f) 29. (a) CN⁻ is a Lewis base (b) CH₃OH is a Lewis base (c) (CH₃)₂CH⁺ is a Lewis acid (d) MgBr₂ is a Lewis acid (e) CH₃BH₂ is a Lewis acid (f) CH₃S⁻ is a Lewis base Let's be smart about the second part. We have three Lewis acids and three Lewis bases. So pair them up and answer the question with just three equations. To reduce clutter, the three lone pairs around each halogen atom have been left out: CH₃ .CH₃ Br H Br H H H CH₃ B + CH₃ H H