CHEM 236 Homework 3 Fall 2024 1 For each of the molecular formulas listed below draw three compounds and calculate the degree of unsaturation a C6H10 DoU 2 11 b C4H8 DoV I c C8H10 DoV 4 x 2 a Rank the stability of the following carbocations Stability 3 1 2 2 b How would the stability of the following carbocations compare to the ones shown above Use resonance and arrow pushing to explain your answer The following carbocations are more stable than those in part a V X W x 3 X X Y S 3 a Predict the major products for the following reactions OH 1 Or I I H Br Br RXn 1 b Draw the mechanisms of the above reactions and explain the unexpected formation of a tertiary alcohol in the second reaction 1 4an 11494 11 OH H H Rxn 2 Arearrangementof carbocation occurs to frset 114an 144 1144 I carbocation L H H Or 14 H a Predict the product of the following bromination reaction y 4 y b How would the product differ if the reaction was performed in H2O instead of CCl4 Draw the mechanism to explain of a 1 Br Br a of Br Bro Br Br T 4 04 Theoxygenin H20 is more nucleophilic thana e OH 45 L a Predict the reactant of the following oxymercuration reduction reaction below b There are four more reactants that could give the same product of the above oxymercuration reduction reaction including E Z isomers draw all of them and name them 5 cis 3 methyl 2 hexene trans 3 methyl 2 hexene trans 3 methyl 3 hexene cis 3 methyl 3 hexene I 2 ethyl 1 panten