Alkyne Exercises
Alkyne Exercises
Alkyne Exercises
These are the homework exercises to accompany the Textmap for McMurry's Organic Chemistry
textbook.
Questions
Q9.1.1
Q9.1.3
A) 4,4-dimethyl-2-pentyne
B) 3-octyne
C) 3-methyl-1-hexyne
D) trans 3-hepten-1-yne
Q9.1.4
Solutions
S9.1.1
A – 3,6-diethyl-4-octyne
B – 3-methylbutyne
C – 4-ethyl-2-heptyne
D – cyclodecyne
S9.1.2
2 possible isomers
S9.1.3
S9.1.4
No. A triply bonded carbon atom can form only one other bond and has linear electron geometry
so there are no "sides". Allkenes have two groups attached to each inyl carbon with a trigonal
planar electron geometry that creates the possibility of cis-trans isomerism.
Questions
Q9.4.1
What alkyne would you start with to gain the following products, in an oxidation reaction? Keep
in mind resonance.
Q9.4.2
Propose a reaction scheme for the following compound starting from the alkyne and showing
required reagents and intermediates.
Solutions
S9.4.1
S9.4.2
Questions
Q9.5.1
Usng any alkyne how would you prepare the following compounds:
pentane, trans-4-methyl-2-pentene, cis-4-methyl-2-pentene.
Solutions
S9.5.1
Questions
Q9.7.1
If OH- has a pKa of 14.00 in water, what pKa be required to deprotonate OH-?
Solutions
S9.7.1
Questions
Q9.8.1
Q9.8.2
Propose a synthetic route to produce 2-pentene from propyne and an alkyl halide.
Solutions
S9.8.1
S9.8.2
Questions
Q9.9.1
A – cis-3-hexene
B – 3,4-dibromohexane
C – 3-hexanol
Q9.9.2
Starting with acetylene and any alkyl halides propose a synthesis to make (a) pentanal and (b)
hexane.
Solutions
S9.9.1
S9.9.2