Organic Chemistry 331 – Sapling Learning CH 10

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Indicate the general type of reaction represented in each the following reactions:

Classify the mechanism as a substitution, elimination, or addition reaction.

What product(s) are expected in the ethoxide-promoted β-elimination reaction of 2-bromo-2,3-dimethylbutane? Omit ions, salts, and ethanol from your response.

In regard to the E2 mechanism, rank the leaving groups in order of increasing reaction rate.

For the following dehydrohalogenation (E2) reaction, draw the major organic product(s), including stereochemistry.

For the following dehydrohalogenation (E2) reaction, draw the major organic product.

For the following dehydrohalogenation (E2) reaction, draw the major organic product(s), including stereochemistry.

Add one curved arrow to each reactant box below to illustrate the movement of electrons in the E1 reaction. (In the second box, there will be a total of two curved arrows, one of which is drawn for you.)

For the following dehydrohalogenation (E2) reaction, draw the Zaitsev product(s), showing the stereochemistry clearly. Show the product stereochemistry clearly. If there is more than one organic product, both products may be drawn in the same box.

For the following dehydrohalogenation (E2) reaction, draw the Zaitsev product(s), showing the stereochemistry clearly. If there is more than one organic product, both products can be drawn in the same box.

For the following dehydrohalogenation (E2) reaction, draw the Zaitsev product(s) resulting from elimination involving C3-C4 (i.e., the carbon atoms depicted with stereobonds). Show the product stereochemistry clearly. If there is more than one organic product, both products may be drawn in the same box. Ignore elimination involving C3 or C4 and any carbon atom other than C4 or C3.

Draw the alkyne formed when 2,3-dichloropentane is treated with an excess of strong base such as sodium amide.

Determine whether each of the following reactions occur through an SN1, SN2, E1, or E2 mechanism.

Consider the following pair of reactions. Predict the type of elimination mechanism, predict which reaction of the pair will occur at the fastest rate, and draw the correct organic product.

Select the mechanism(s) where the concentration of the nucleophile/base has no effect on the reaction rate.

Unsymmetrical ethers can be made by the Williamson synthesis, in which an alkoxide ion reacts with an alkyl bromide. Draw the structure of the alkoxide and the alkyl bromide needed to produce 2-ethoxy-2-methylpropane (a.k.a t-butyl ethyl ether), shown below. Show charges where appropriate.

Draw the neutral organic products.

Draw the neutral organic products.

Draw an alcohol and an alkyl bromide that could be combined to give the ether shown.

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