Organic Chemistry 331- Sapling Learning CH 9

Add curved arrows to the reactant side of the following SN2 reaction.

Add curved arrows to the reactant side of the following SN2 reaction to indicate the flow of electrons. Draw the product species to show the balanced equation, including nonbonding electrons and formal charges.

Select the properties of the SN2 reaction mechanism.

Rank the SN2 reaction rate of the following species.

Given the following single-step reaction, draw the curved-arrow mechanism.

Select the properties of the SN1 reaction mechanism.

For the following SN1 reaction, draw the major organic product, identify the nucleophile, substrate, and leaving group, and determine the rate limiting step.

Select the correct IUPAC name for the following organic substrate, including the R or S designation where appropriate, and draw the major organic product(s) for the SN1 reaction. Include wedge/dash bonds on a stereocenter.

Rank the following carbocations in order of decreasing stability.

Add one or more curved arrows to show the movement of electrons in the following reaction:

Select the correct IUPAC name for the following organic substrate, including the R or S designation where appropriate, and draw the major organic product(s) for the SN1 reaction. Include wedge/dash bonds and H on a stereocenter.

Draw the major organic product for the following reaction:

Draw the major organic substitution product for the following reaction:

unknown

For a certain substitution reaction, the rate of substitution is found to be independent of both the concentration and the nature of the nucleophile. What is the most likely mechanism?

Draw the major organic product for the following reaction:

Add one or more curved arrows to show the movement of electrons in the following reaction:

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

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

Rank the relative rates of the following alkyl halides in an SN2 reaction. (Drag the structure to the appropriate box, fastest on the top to slowest on the bottom.)

Rank the SN1 reaction rates for the following compounds:

Rank the relative rates of the following alkyl halides in an SN1 reaction. (Drag the structure to the appropriate box, fastest on the top to slowest on the bottom.)

Rank the SN1 reaction rates for the following compounds:

Does the carbocation intermediate in the hydrolysis of 2-bromo-3-methylbutane rearrange by way of a hydride shift, methyl shift, or neither?

Does the carbocation intermediate in the hydrolysis of 2,2-dimethyl-1-iodocyclohexane rearrange by way of a hydride shift, methyl shift, or neither?

Draw the major, neutral organic product obtained if: a) the reaction proceeds by the SN1 mechanism; b) the reaction proceeds by the SN2 mechanism.

A researcher attempts a substitution reaction with two different reagents, water or hydroxide ion, to see which route is better. Draw the major, neutral organic compound recovered from each attempted substitution reaction below. (If no reaction, draw the starting material. Disregard elimination.)