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Magazine Chapter 7: Q39P (page 315)
What is the major product of the reaction of 1 mol of propyne with each of the following reagents?
a.HBr (1 mol)
b.HBr (2 mol)
c.Br2(1 mol)/CH2Cl2
d.Br2 (2 mol)/CH2Cl2
e.aqueous H2SO4, HgSO4
f.R2BH in THF followed byH2O2/HO- /H2O
g.excess H2, Pd/C
h.H2/Lindlar catalyst
i.sodium amide
j.the product of part i followed by1-chloropropane
Short Answer
Step by step solution
Step 1:
Major product of the reaction of 1 mol of propyne withHBr (1 mol) forms 2-bromoprop-1-ene.
Step 2:
Major product of the reaction of 1 mol of propyne withHBr (2 mol)
forms 2,2-dibromopropane.
Step 3:
Major product of the reaction of 1 mol of propyne withBr2(1 mol)/CH2Cl2
forms (E)-1,2-dibromoprop-1-ene.
Step 4:
Major product of the reaction of 1 mol of propyne withBr2 (2 mol)/CH2Cl2
forms 1,1,2,2-tetrabromopropane.
Step 5:
Major product of the reaction of 1 mol of propyne withaqueous H2SO4, HgSO4forms propan-2-one.
Step 6:
Major product of the reaction of 1 mol of propyne withR2BH in THF followed by H2O2/HO- /H2Oforms propionaldehyde.
Step 7:
Major product of the reaction of 1 mol of propynewith excess H2, Pd/C
formspropane.
Step 8:
Major product of the reaction of 1 mol of propynewith H2/Lindlar catalyst
formsprop-1-ene.
Step 9:
Major product of the reaction of 1 mol of propyne with sodium amideforms prop-1-yn-1-ide.
Step 10:
Major product of the reaction of 1 mol of propyne withthe product of part i followed by 1-chloropropaneforms hex-2-yne.
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