Dr. Sereda I was going through last years quiz and I was wondering what you were referring to when you asked to list the “alkylating agent”  in the reaction that produces 5-methyl-2-hexyne from propyne. I thought it might be something such as 1-bromo-3-methylpropane or 1-iodo-3-methylpropane, but I am not sure. (Alkylating group is a group introducing alkyl to another molecule. Both your examples fit this definition, because they introduce the iso-butyl group to the nucleophile generated from propyne. - GS).

What would the mechanism look like for a reaction between 1-methylcyclohexene and Br2? (Addition through bromonium. - GS).- How do we determine the stereoselectivity with the methyl group on the ring? (Trans- with respect to bromonium. - GS). And could this product be isolated as an enantiomer? (Yes, because it is chiral. - GS).

This is slightly conceptual, but Markovnikov’s rule allows us to determine the regioselectivity of an addition product, correct? (Yes, if we do not need to choose between several C=C bonds. - GS).

In hydroxylation and epoxidation of alkenes, what reagents would be useful for anti addition? (1. Peroxoacid. 2. OH- - GS).  And for syn? (OsO4 or MnO4- - GS).  Do these affect Markovnikov’s rule? (There is no connection. - GS).

Can you list the exceptions to Markovnikov’s rule?  Can we do examples in class? (1. Reversal of stabilities of carbocations because of strong electron withdrawing substituents at the more substituted carbon. 2. Change of the reaction mechanism, such as shift to the free-radical mechanism. - GS).

How do we compare Hoffman’s rule and Zaitsev’s rule? (Hoffman’s postulate tells us when we should and when we should not approximate transition states by intermediates to justify Zaitsev’s and any other rule. - GS).

Could we go over the epoxidation mechanism again? (A peroxo-acid forms a 5-membered intermediate, which transfers oxygen to the C=C bond. - GS).

If you have an addition reaction that does not follow the Markovnikov rule, will it produce free radicals as well? (Anti-Markovnikov addition most likely proceeds by a free-radical mechanism, which produces free radicals only at intermediate steps. - GS).

Dr. Sereda, what is the product of epoxidation (An epoxide - GS). and what is its significance? (It is an active electrophilic ether. Very useful in organic synthesis, in particular, synthesis of primary alcohols, trans-diols, and epoxide resins. - GS). What kind of reactant would have to be present to make a trans-diol? (Epoxide and OH- - GS).

I know we have not covered oxymercuration demercuration, but when we do could we go over the reduction mechanism between NaBH4 and the less substituted Mercury Acetate? Thanks. (First, H- replaces the acetate ligand at Hg, and then shifts to carbon, breaking both H-Hg and C-Hg bonds with possible intermediacy of the alkyl free radical (JACS, 1974, 96,3,870). - GS).

How do we know where the molecule will split when it undergoes cracking? (Preferably - to form the most stable free radical. - GS).

What is a radical chain process? (It is a process involving the chain propagation step: a free radical as both a starting particle and a resulting product. - GS).

Why are heats of combustion important? (They tell us how stable the compound is and how much energy it can produce. - GS).

In class, can you go over “Chair flips?” (OK https://www.youtube.com/watch?v=6VUU-_JExMs . - GS).