Write the product of the two reactions shown below. In the first step indicate if the product is meso or is formed as a racemic mixture. Indicate whether final structure in the second reaction is cis or trans. Br-Br H LDA, THF solvent

QUESTION #4 Draw the step-by-step mechanism for the following SN1 reaction. Be sure to draw arrows for the movement of ALL electrons. Show any and all intermediates. You do not have to show stereochemistry for this question. CH3OH heat Br OCH3

Start with condensed structural formula CH3-CH(OH)-CH(CH3)-CH2-CH(CH3)2 and react it first with H2SO4 and high heat, to produce a major substrate product. Then, take that major substrate product, and use it as the substrate of the next reaction, by reacting it with Br2 (in the presence of CH2Cl2 solvent), to produce the FINAL MAJOR substrate product.   The complete correct condensed structural formula for the major substrate product after reaction step 1 is  ___________.  (If no new product is formed in this step, type "no reaction.") The complete correct condensed structural formula for the final major substrate product (after reaction step 2) is __________ .  (If no new product is formed in this step, type "no reaction.")

Draw a structural formula for the major organic product of the reaction shown below. Br Ca -85 -CuLi • Consider E/Z stereochemistry of alkenes. • Do not show stereochemistry in other cases. • You do not have to explicitly draw H atoms. • Do not include organocopper or inorganic ion by-products in your answer. Sn [F ChemDoodleⓇ

Draw the structure of the major organic product of the reaction below. Zn(Cu) CHCH3 + CH212 • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Show stereochemistry in a meso compound. •If the reaction produces a racemic mixture, just draw one stereoisomer.