OpenStax Organic Chemistry 10th Edition – Chapter 9 Student Solutions Manual (SSM)

OpenStax Organic Chemistry: A Tenth Edition Student Solutions Manual

Chapter 9 – Alkynes: An Introduction to Organic Synthesis
Solutions to Problems
9.1 The rules for naming alkynes are almost the same as the rules for naming alkenes. The
suffix -yne is used, and compounds containing both double bonds and triple bonds are
-enynes, with the double bond taking numerical precedence.

(a) (b)




(c) (d)




(e)




9.2




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, OpenStax Organic Chemistry: A Tenth Edition Student Solutions Manual



9.3 Markovnikov addition is observed with alkynes as well as with alkenes.
(a)


(b)




(c)




Two products result from addition to an internal alkyne.

9.4



This symmetrical internal alkyne yields only one product.




Two ketone products result from hydration of 2-methyl-4-octyne.

9.5 (a)




(b)




The desired ketone can be prepared only as part of a product mixture.




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, OpenStax Organic Chemistry: A Tenth Edition Student Solutions Manual



9.6 Remember that hydroboration yields aldehydes from terminal alkynes and ketones from
internal alkynes.

(a)



(b)




9.7
(a)




(b)




9.8 The correct reducing reagent gives a double bond with the desired geometry.

(a)




(b)




(c)




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