For the following set of E2 reactions, draw the major organic product and indicate which reaction occurs at the faster rate (same expected products for both, can draw once) CH3 H3C H3C CH3 -CH3 S=O CH3 CH3O S=O

Consider the SN2 reaction of butyl bromide with OH- ion. CH3CH2CH2CH2B + OH- → CH3CH2CH2CH2OH + Br Assuming no other changes, what effect on the rate would result from simultaneously doubling the concentrations of both butyl bromide and the OH- ion? Draw the curved arrow mechanism for the SN1 reaction of methanol with tert-butyl iodide. Next, draw an Energy vs. Reaction Coordinate diagram for this reaction, labeling all transition states as "TS" and intermediates as appropriate for those drawn in the mechanism above, showing the relative energies on the diagram.

Draw the product of the E2 reaction shown below. Include the correct stereochemistry. Ignore any inorganic byproducts. I H H3CH₂C CH3 Br LOCH3 H NaNH, Drawing I I

Draw the reaction mechanism of this reaction and state whether it is a SN1 or SN2 reaction.

5. For the following reactions, draw the complete, detailed mechanism (including curved arrows) for an E2 mechanism and an E1 mechanism. If more than one possible product can be produced from the same type of mechanism, draw the complete mechanism that leads to each one. Pay attention to double bond stereochemistry. E2 mechanism(s) CI E1 mechanism(s) CI E2 mechanism(s) Br 'CH3 E1 mechanism(s) Br "CH3 NaOH NaOH KO'Bu KO'Bu

Draw the major product of the following sequence of reactions. If the reaction is likely to give you a mixture of ortho and para disubstituted compounds you should assume that they can be separated; continue the synthesis with either one. If so, draw the intermediates as well. CH3 K₂Cr₂07 Cl₂, AlCl3 H2SO4

4. Each of the following alkyl bromides gives only one product in via an E2 mechanism. Provide the mechanism and the product for each of the following reaction. Draw Newman projections to determine the E/Z diastereomers. Br E2 Br E2

11. Determine whether each reaction occurs by an SN2, SN1, E1, and/or E2 reaction. Provide a detailed mechanism with curved arrows and the major product(s). OMs Br Br OH мон OH NaSH DMF NaOH H₂O, heat LDA DMF NaOH H₂O, heat HBr H, H₂O heat

Given that an E2 reaction proceeds with anti periplanar stereochemistry, draw the products of each elimination. The alkyl halides in (a) and (b) are diastereomers of each other. How are the products of these two reactions related? Recall from Section 3.2A that C6H5 −is a phenyl group, a benzene ring bonded to another group.

Q12. (1-bromoethyl)benzene 1 udergoes an elimination following an E1 mechanism. Fill in the following synthetic scheme by drawing the structure of intermediate 2 and product 3. The chemical formula of product 3 is provided as guidance. CH; RDS Br C3Hg E1 2 3