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Chapter 7: Q37P (page 315)

How can the following compounds be synthesized, starting with a hydrocarbon that has the same number of carbons as the desired product?

Short Answer

Expert verified

Pent-1-ynereacts with R2BH and OH-, H2O2 and H2O to form pentanal.

Step by step solution

01

Step 1:

Pent-1-ynereacts with R2BH and OH-, H2O2 and H2O to form pentanal.

02

 

But-1-ene reacts with BH2 and OH-, H2O2and H2O to form butan-1-ol.


03

Step 3:

The highest yield of desired ketone will come from this symmetrical alkyne.

The reaction does not require a mercuric ion catalyst because the reactant is not a terminal alkyne.

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Most popular questions from this chapter

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

Draw a condensed structure for each of the following:

a.2-hexyne

b.5-ethyl-3-octyne

c.methylacetylene

d.vinylacetylene

e.methoxyethyne

f.sec-butyl-tert-butylacetylene

g.1-bromo-1-pentyne

h.5-methyl-2-cyclohexenol

i.diethylacetylene

j.di-tert-butylacetylene

k.cyclopentylacetylene

l. 5,6-dimethyl-2-heptyne

Drawing on what you know about the stereochemistry of alkene addition reactions:

a. Write the mechanism for the reaction of 2-butyne with one equivalent of Br2.

b. Predict the configuration of the product of the reaction.

What is the molecular formula for a monocyclic hydrocarbon with 14 carbons and 2 triple bonds?

Identify the electrophile and the nucleophile in each of the following reaction steps. Then draw curved arrows to illustrate the bond-making and bond-breaking processes.
See all solutions

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