(Z) 1-cyclopentyl-3,6-dimethylhept-3-en-1-yne

(E) 1-cyclopentyl-3,6-dimethylhept-1-yn-3-ene

(Z) 1-cyclopentyl-4,7-dimethylhept-4-en-2-yne

(E) 1-cyclopentyl-3,6-dimethylhept-3-en-1-yne

4-(1-bromopropyl)-1-hexen-5-yne

4-allyl-5-bromo-1-hexyne

3-(1-bromopropyl)-5-hexen-1-yne

5-bromo-4-ethynyl-1-heptene

relatively nonpolar

nearly insoluble in water

less dense than water

insoluble in most organic solvents

1-pentyne

2-hexyne

3-pentyne

1-butyne

2 and 3

1 and 2

3 and 4

4 and 5

but-1-yne and ethane

water and but-1-yne

water and ethane

but-1-yne and but-2-yne

The strong base deprotonates the terminal alkyne and removes it from the equilibrium

The resonance favors the formation of the terminal rather than internal alkyne

The positions of the Cl atoms induce the net formation of the terminal alkyne

The terminal alkyne is not favored in this reaction

2-heptyne

(Z)-2-heptene

(Z)-3-heptene

(E)-3-heptene

aldehyde

ketone

diol

ether