Question

4. Reaction Fill-ins! Predict the product(s) OR starting material of the following reactions. Remember Hydride shifts are possible if when a more stable carbocation can exist (depending on reaction mechanism)! Put your answers in the indicated boxes. H2SO4 (cat.), H20 а. 1.4-product 1.2-product Br Br HBr b. Br Major product Minor produt Minor product HCI C. 1,2-product 1,4-product HI он MAJOR prod Minor prod. e. Draw the FULL electron-pushing mechanism for the reaction in part a above, INCLUDING ALL resonance contributors. Explicitly label all formal charges and or electron pairs. Label the nucleophile and electrophile in each reaction step

Answer 1

4(a) H₂SO4 Cat), H₂O 61,2)-product H I Nucleophillic attack by T-bond on Proton Nucleophillic attack by to on electrophillic C-atom. Proton Abstraction. (12) - Product)

OM 1 114) - Product

Н - В (1,2)-Hydride shift A - attack by Ti-bond of alkene on proton. (1, 2) - Hydride shift. Nucleophillic attack by Br on electrophillic C-atom. 117 J: Bri (Major peoduel)) Il Minor product) Н o g (1.31-iya nuk shift (1, 2)-Hydrich shift JB (Minon product)) is - Most stable carbocation as it stabilized by Conjugation with Phenyl group

-C1 (1, 2)-product | H-Cl (1,4)-product -Ho - Protonation of oxygen atom. Removal of water Nucleophillic attack by I to give minor product (1, 2) - Hydride Shift (Minion Product) to give (1,2 -Hydride shift 3° Cabocation Nucleophillic attack by give mapor product I to (Marjor product