compounds

compounds

1. For the following compounds, write structural formulas and IUPAC names for all possible isomers having the identical number of multiple bonds:
a. C5H8 (two double bonds)
b. C6H10 (one triple bond)
2. Write a structural formula for each of the following compounds:
a. 1,3-heptadiene
b. 3-bromocyclohexene
c. allyl bromide
d. 2,3-dimethyl-1,3-cyclohexadiene
3. Which of the following compounds can exist as cis-trans isomers? If such isomerism is possible, draw the structures in a way that clearly illustrates the geometry.
a. 2-butene
b. 1-bromobutene
c. 1-chloro-1,3-pentadiene
4. Write an equation for the reaction of 3-methyl-2-pentene with each of the following reagents:
a. hydrogen bromide
b. BH3 followed by H2O2, OH¯
c. hydrogen (Pt catalyst)
d. KMnO4, OH¯
e. bromine
f. H2O, H+
5. What reagent will react by addition to what unsaturated hydrocarbon to form each of the following compounds?

6. Which of the following reagents is an electrophile? Which is a nucleophile?
a. Br¯
b. BF3
7. Explain in your own words why the water molecule can act either as an electrophile or as a nucleophile.
8. The acid-catalyzed hydration of 1-ethylcyclopentene gives 1-ethylcyclopentanol. Write every step in the mechanism of this reaction.
9. Draw the resonance contributors to the carbocation Does the ion have a symmetric structure?
10. Adding one equivalent of sulfuric acid to 2,4-hexadiene gives two products. Give the structures, and write all the steps in a reaction mechanism that explains how each product is formed.
11. Predict the product of this Diels-Alder reaction.

12. Write an equation that clearly shows the structure of the alcohol obtained from the sequential hydroboration and H2O2/OH¯ oxidation of 1-methylcyclohexene.
13. Write equations to show how 2-methyl-1-pentene could be converted to
a. 2-hydroxy-2-methylpentane
b. 1-hydroxy-2-methylpentane
14. Write equations for the following reactions:
a. 2-pentyne + H2 (1 mol, Lindlar’s catalyst)
b. 1-butyne + HBr (2 mol)

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