Checking my answer, there was difference with solution. (organic chemistry smith 5th ed 2.47P (d)) Solution said 'the acid base reaction between pentyne and ammonia is product way because pka of pentyne is 25, ammonia is 38 so

Chemistry for Today: General, Organic, and Biochemistry
9th Edition
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Chapter14: Aldehydes And Ketones
Section: Chapter Questions
Problem 14.55E: The addition of water to aldehydes and ketones occurs rapidly, although it is not thermodynamically...
icon
Related questions
icon
Concept explainers
Question
100%

Checking my answer, there was difference with solution.

(organic chemistry smith 5th ed 2.47P (d))

Solution said 'the acid base reaction between pentyne and ammonia is product way because pka of pentyne is 25, ammonia is 38 so pentyne will be deprotanted by ammonia.' 

but I think (and as written in the book) NH4+ is stronger acid than pentyne and acid-base reaction works when reactant is stronger acid than product conjugate acid. It isn't match that pentyne makes NH4+.

who is incorrect?

Expert Solution
steps

Step by step

Solved in 3 steps with 1 images

Blurred answer
Knowledge Booster
Ionic Equilibrium
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Chemistry for Today: General, Organic, and Bioche…
Chemistry for Today: General, Organic, and Bioche…
Chemistry
ISBN:
9781305960060
Author:
Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:
Cengage Learning