In the following reactions which products are correctly shown? CH3 Br CH2 HBr OH Ether Br NBS hu, CCL4 Br Mg CH,CH,CH,CHB CH3 Ether H20 CH;CH,CH-CH CH3 Li 0.5 Cul CH;CH2CH;CH2BT (CH;CH,CH;CHXCULİ Pentane

ОН 1. H(OAc)2, На0 2. NABH4 .CH3 CH3 H2C H3C Acid-catalyzed addition of water to an alkene yields an alcohol with Markovnikov regiochemistry. The electrophilic H adds to the sp carbon with the most hydrogens to yield the most stable carbocation intermediate, which then adds water to give the product alcohol. Because a carbocation intermediate is formed, rearrangements can occur prior to the addition of water. To avoid the possibility of rearrangement and still give a Markovnikov alcohol, alkenes can instead be treated with mercury(II) acetate in aqueous THF and then subsequently reduced with sodium borohydride. This reaction proceeds through a cyclic mercurinium ion intermediate which cannot rearrange. Water adds to the cyclic intermediate at the most substituted carbon to give an organomercury alcohol. The reduction step with sodium borohydride is complex and involves radicals. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing…

Draw the products of the following reactions, indicating both regiochemistry and stereochemistry when appropriate.

For each reaction below suggest structures for alkenes that give the indicated reaction products. There may be more than one answer in some cases