Solved: In each reaction box, place the best reagent and conditions

In each reaction box, place the best reagent and conditions from the list below.

Problem:

In each reaction box, place the best reagent and conditions from the list below.

Solution:

Note that the condition of the double bond changed. The moving functionality includes optional addition and elimination reactions.

• When given an alkene: start with the addition
• When given RX or ROH: start with the elimination

Step 1: We’re given an alkene which means the first step should be addition.

We can do hydrohalogenation (which follows Markovnikov’s rule) using HBr.

Step 2: The alkene went from disubstituted to trisubstituted, which corresponds to a Zaitsev elimination. This can be done using a small strong base such as CH3CH2O– (ethoxide ion, an alkoxide).

Therefore, the best reagents and conditions are:

1. HBr (hydrohalogenation)
2. CH3CH2O– (elimination)

In each reaction box, place the best reagent and conditions

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