H3O+ HO Inspect the final product and select all the reasons why acid in water was chosen to effect the following transformation instead of the other reagents.

For the reaction shown, draw the major organic product(s) and select the best name for the organic reactant. If there is more than one major product, both may be drawn in the same box. Indicate stereochemistry with wedge-and-dash bonds. HBr H > Feedback The HBr adds to the alkene using Markovnikov's rule, giving a planar carbocation. The carbocation will react with the bromide ion to give a pair of diastereomeric products. Why? Determine E vs. Z alkenes by analyzing which substituents have the highest priority. If the highest priority substituents are on the same side of the alkene, it is Z.

Write a mechanism that accounts for the formation of ethyl isopropyl ether as one of the products in the following reaction. CI OEt HCI EtOH Write the mechanism for step one of this reaction. Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. Write the mechanism for step two of this reaction (where the product of step one reacts with the solvent, ethanol). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. Write the mechanism for the last step of this reaction (formation of ethyl isopropyl ether). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. CI will act as the base in this reaction.

Draw the products of the three step reaction sequence shown below. Ignore inorganic byproducts. If the reaction results in a mixture of ortho and para isomers, draw only the para-product.

The synthesis above used bromoethane, but acetylene is the only allowed source of carbon atoms. Using the reagents given, identify a synthetic route for the production of bromoethane from acetylene. The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer.

methanol + CH3OH Suppose you were told that the above reaction was a substitution reaction but you were not told the mechanism. Evaluate the following categories to determine the reaction mechanism and then draw the structure of the major organic product. Type of alkyl halide: Type of nucleophile: Solvent: Is the product racemic?

Convert 2-pentanol into 2,3-dibromopentane. Draw structures of the starting material (2-pentanol) and final product (2,3-dibromopentane), and show the two reactions needed for this synthesis. Include the structure of the intermediate compound, and the reagents and conditions for each reaction. Then explain why 1,2-dibromopentane would not be a significant product of this synthesis.

6) You have decided to repeat the reaction from Question 5 using a slightly different alkene starting material. You now observe 3 products, and you suspect that your major product (Product A) is the result of a carbocation rearrangement. Draw the mechanism for the formation of Product A and indicate which type of carbocation rearrangement has occurred. H₂O H₂SO4 A OH 67% Major Product B OH 32% Minor Product C 1% OH

What reagents are needed to carry out this reaction? CH;CH,CH2CCH PCC in methylene chloride Sia2BH and then basic hydrogen peroxide Aqueous acid and mercury sulfate MCPBA and then Swern Oxidation Question 10 What is the intermediate that forms during this reaction? CH;CH,CH,CCH O an enol an epoxide an alkoxide a carbanion

All electrophilic aromatic substitution reactions occur via a two-step mechanism: addition of the electrophile to form a resonance-stabilized carbocation, followed by deprotonation by a base. In the step shown below, loss of a proton to form the substitution product was drawn using the resonance structure with the + 1 formal charge at the ortho position to the carbon bonded to the electrophile. Redraw the step shown with the other two resonance structures and use curved arrows to show how these other two resonance structures can be converted to the substitution product by removal of a proton with the base shown. Part: 0/2 Part 1 of 2 H :CI-AICI, Draw the mechanism that generates the final substitution product with the +1 formal charge at the para position. Cl HC1 AICI3