Change the structure below to show the most stable form of this carbocation intermediate. X 5

HBr ? What is the structure of the major product of the reaction? °୪ Br .8 Br ○ Br -Br

Consider this reaction: Br CH;OH Br-Br H3CO The mechanism proceeds through a first cationic intermediate, intermediate 1. Nucleophilic attack leads to intermediate 2, which goes on to form the final product. In cases that involve a negatively charged nucleophile, the attack of the nucleophile leads directly to the product. Br + CH3OH Br Intermediate 1 Intermediate 2 (product) In a similar fashion, draw intermediate 1 and intermediate 2 (final product) for the following reaction. OH + Br2 + HBr Br racemic mixture

Draw the most stable resonance form for the intermediate in the following electrophilic substitution reaction. LOCH3 LOCH3 HNO3 / CH3CO₂H O₂N • You do not have to consider stereochemistry. • Include all valence lone pairs in your answer. ● In cases where there is more than one answer, just draw one.

4. A student wants to make molecule B with the following reaction below. Instead of molecule B, a different molecule is made. Give the structure of this compound. HO HO OH H₂NOH * HO N OH HO B OH

Draw the most stable resonance form for the intermediate in the following electrophilic substitution reaction. CH3 CH3 CH3CI / AICI3 • H3C • You do not have to consider stereochemistry. Include all valence lone pairs in your answer. In cases where there is more than one answer, just draw one.

2. The following carbocation is generated as an intermediate in the addition of H-Br to an alkene. Draw the structure of all possible alkenes that could have formed this intermediate.

What is (are) the product(s) of the following reaction? NHCOCH3 HNO3 H2SO4 NHCOCH3 O,N. NHCOCH3 NHCOCH3 `NO2 O2N II II

Which of the following carbocations is the most stable? II IV II O Iv

Chemistry 4. Draw the correct product (may be multiple competing products) and label each of them as the product of E1, E2, SN1, or SN2. Br oner Br- OTS KCN DMSO NaOH H₂O, heat H₂O CH,CH,ONa CH₂CH₂OH NaSH DMSO KOH DMSO NINH, NH₂ NH₂ please explain