Organic Chemistry 331- CH 6

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Predict the organic product of the following reaction. Include hydrogen atoms in your structure. When drawing hydrogen atoms on a carbon atom, either include all hydrogen atoms or none on that carbon atom, or your structure may be marked incorrect.

Predict the product for the following reaction: When drawing hydrogen atoms on a carbon atom, either include all hydrogen atoms or none on that carbon atom, or your structure may be marked incorrect.

Draw the structure of the alkene that reacts with HBr to give the following alkyl bromide as the major organic product.

For the following reaction: 1) Add curved arrows for the first step.
2) Draw both the organic and inorganic intermediate species. Include nonbonding electrons and charges, where applicable. Include hydrogen atoms.

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For the following reaction, draw the major organic product and select the correct IUPAC name for the organic reactant. If there is more than one major product, both may be drawn in the same box. When drawing hydrogen atoms on a carbon atom, either include all hydrogen atoms or none on that carbon atom, or your structure may be marked incorrect.

Select the correct IUPAC name for the organic reactant:

Consider the acid-catalyzed hydration of 3-methyl-1-butene. For each of the four steps, add one or two curved arrows to the reactant side to show the mechanism.

Predict the organic product of the following reaction and include hydrogen atoms in your structure.

Predict the neutral organic product of the following reaction. When drawing hydrogen atoms on a carbon atom, either include all hydrogen atoms or none on that carbon atom, or your structure may be marked incorrect.

Draw the structures of the alkene and the alcohol that react to give the following ether as the major organic product.

Predict the two major organic products of the following reaction. Include hydrogen atoms in your structure. (HI behaves as an HX reagent.)

For the following reaction, draw the major organic product and select the correct IUPAC name for the organic reactant. If there is more than one major product, both may be drawn in the same box. When drawing hydrogen atoms on a carbon atom, either include all hydrogen atoms or none on that carbon atom, or your structure may be marked incorrect.

Select the correct IUPAC name for the organic reactant:

Draw the structures of two stereoisomeric alkenes that would give 3-hexanol as the only major product of hydroboration followed by treatment with alkaline H2O2:

Draw the major organic product for each of the following hydroboration-oxidation reactions. Disregard stereochemistry.

Show the mechanism for the following reaction conducted at -5 °C in CCl4: cyclohexene bromine yields a dibromocyclohexane Draw structures – including charges and electrons – and add curved arrows. Details count.

Predict the product of the following reaction. Draw all hydrogen atoms.

Draw the structure of 1,2-epoxypentane.

Choose the correct reactants and/or catalysts to complete the following reactions:

Draw the product of the following reaction. Show all the hydrogen atoms in your structure.

Draw the three alkenes, each of formula C5H10, that will form 2-methylbutane upon hydrogenation.

For the following hydrogenation reaction, draw the correct organic product and select the correct IUPAC name for the organic reactant. When drawing hydrogen atoms on a carbon atom, either include all hydrogen atoms or none on that carbon atom, or your structure may be marked incorrect.

For the following hydrogenation reaction, draw the correct product and select the correct IUPAC name for the organic reactant. (Ignore product stereochemistry in your answer.) When drawing hydrogen atoms on a carbon atom, either include all hydrogen atoms or none on that carbon atom, or your structure may be marked incorrect.

Select the correct IUPAC name for the organic reactant.

For the following reaction, draw the major organic product(s) and select the correct IUPAC name for the organic reactant. Stereoisomers are expected, so draw both. Hint: consider rearrangement possibilities. When drawing hydrogen atoms on a carbon atom, either include all hydrogen atoms or none on that carbon atom, or your structure may be marked incorrect.

Predict the product of treating the given alkene with the reagent shown below. Only draw one enantiomer if more than one is possible. Include H\’s on chirality centers.

Predict the oxidation product of treating dihydronaphthalene with the reagents shown below. Only draw one enantiomer if more than one is possible. Include H\’s on chirality centers. (THF = tetrahydrofuran)

Predict the oxidation product of treating the given alkene with the reagent shown below. Include stereochemistry where applicable. Include H\’s on chirality centers. (mCPBA = meta-chloroperoxybenzoic acid)

Identify the reactant, reagent, and solvent used to synthesize the product below.

Part 1: There are several reagents that can be used to effect addition to a double bond, including: acid and water, oxymercuration-demercuration reagents, and hydroboration-oxidation reagents. Inspect the final product and select all the reasons why oxymercuration-demercuration was chosen to effect the following transformation instead of the other reagents.

Part 2: Complete the mechanism for the reaction by adding curved arrows. The reagents chosen for the transformation are: 1) Hg(OAc)2, THF, H2O and 2) NaBH4, OH-. (The acetate ion is a spectator throughout.)

Alkenes can be converted to alcohols by reaction with mercuric acetate to form a β-hydroxyalkylmercury(II) acetate compound, a reaction called oxymercuration. Subsequent reduction with NaBH4 reduces the C-Hg bond to a C-H bond, forming the alkyl alcohol, a reaction called demercuration. Draw the structure of the Hg-containing compound and the final alcohol product formed in the following reaction sequence.

(Partially incorrect)

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