2. Mechanism a. Draw the product of the reaction of (1R,2R)-2-bromocyclopentan-1-ol with NaH. Show a complete mechanism, using curved arrows, for the formation of this product. OH NaH ¹Br b. When the diastereomer, (1R,2S)-2-bromocyclopentan-1-ol, is subjected to these conditions, no reaction occurs. Briefly explain why no reaction takes place. OH & Br

4. Write the mechanism of the following reaction. Use curved arrows to show the movement of electrons in each step. Draw the bromonium ion intermediate emphasizing the major position of positive charge. Draw and write "cis" or "trans" of the high priority groups in the product for full credit + Br-OH, water, NaOH Hi CH3

5. Subjection of 1-bromo-1-methylcyclopentane to the hydrolytic conditions shown leads to a mixture of products. Br -CH3 H₂O heat -CH3 OH -CH3 =CH₂ + H3O+ + Br A B с a. Which alkene do you expect to be most abundant in the product mixture? b. Provide a stepwise mechanism to explain how the alkene labeled C is formed. c. The reaction above is shown with hydronium ion (pK₂~-1.7) and bromide as products rather than HBr (pKa ~ -9). Use acid-base concepts to explain why HBr does not exist when there is an abundance of water.

Propose a structure for the undesired product and explain why this product is formed under these conditions.

2.a. Give the mechanism and product(s) for the reaction below. Be sure to show the initiation step(s). 2.b. How are the products related? Clearly indicate stereochemistry. + HBr HOOH

Propose a mechanism for this transformation. Add any remaining curved arrow(s) to complete step 1 of the mechanism. Modify the given drawing of the product as needed to show the intermediate that is formed in this step. H. P HÖ: HO он + 1-ÖH; F CI + Br + ----

5.

6. Methylcyclopentanol on treatment with HBr gives 1-bromo-1-methylcyclopentane as a major product. Show a detailed mechanism to explain your answer . CH3 H3C Br HBr HO- -H20 2-methylcyclopentanol 1-bromo-1-methylcyclopentane CS Scanned with CamScanner

what product would you expect from the SN1 reaction of (S)-3-methyloctan-3-ol[(S)-3-hydroxy-3-methyloctane] with HBr? Show the stereochemistry of both starting materail and product.

How many possible regioisomers are possible from the following E1 reaction? How many of these regioisomers have corresponding stereoisomers (ie. E/Z isomers)? Explain. Br H₂O, heat