10.11: Additional Exercises

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Alkyne Reactions

10-1 Predict the product of these following reactions:

10-2 Using acetylene as the starting material, show how you would synthesize the following compounds

b) but-2-yne

10-3 Identify the reagents needed to turn hex-1-yne into the following compounds

a) hexane

b) oct-3-yne

c) cis-hept-2-ene

d) trans-hept-2-ene

e) 2,2-dibromohexane

f) 1-bromohexene

10-4 Show how you would accomplish the following synthetic transformations.

10-5 Deduce the structure of each unknown from the information given.

a) Upon catalytic hydrogenation, unknown A yields pentane. Ozonolysis of A yields butanoic acid, HOOC(CH₂)₂CH₃ and CO₂. Draw the structure of compound A

b) Upon catalytic hydrogenation, unknown B yields pentane. Ozonolysis of B yields acetaldehyde, CH₃CHO, and propionaldehyde, CH₃CH₂CHO.

10-6 Use compound A from the previous problem (10-5) and any additional reagents you may need to synthesize the following compound.