Select correct and most relevant mechanism for each of the following reaction. Hint: Review Chapter 11.4. Mechanism A: nucleophilic attack proton transfer CH₂ 5 Jy g H proton Br dilute H-Br: transfer = Mechanism B: dilute HBr Mechanism C: proton transfer nucleophilic attack H CH3 H CH3 Br 5-8-8-8 z z :Br = dilute H-Br: dilute H-Br: OA O Mechanism D: B nucleophilic attack dilute H-Br: = Br secondary carbocation proton disassosiation CH₂ primary carbanion Br: H.O HCH₂ tertiary carbocation hydrogen migration (rearrangement) proton disassosiation dilute H-Br: proton transfer H-Br: ** elimination H H. Br: CH₂ H H-Br: + tertiary carbocation proton transfer CH₂ elimination H-Br: proton transfer, Br nucleophilic attack Br-H secondary carbanion proton transfer Br dilute H-Br: Bri nucleophilic attack = H H H H₂ CH3 .Br Br CH3 tertiary carbocation

1. H3C H CH3 2. H3C + Br CH3 H3C H excess NH3 NH4CI H H NH2 C2H5 N-C₂H5 C2H5 + C2H5 H-N-C2H5 Br C2H5 a Proton transfer b Lewis acid/base e Electrophilic addition h = Syl Nucleophilic substitution f El Elimination i = SN2 Nucleophilic substitution c Radical chain substitution g E2 Elimination j Electrophilic aromatic substitution d Radical chain addition Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - j for your answers.

10:47 AM Sun Nov 27 ← Question 28 of 41 Draw the Alkyl Halide Rea nt @72% Draw an alkyl halide that produces ONLY the following alkene in an E2 elimination. Ignore any inorganic byproducts. Strong Base Submit

H,SO4 1. H20 n-Bu Na NH2 2. -CN CN 2 Br NaBr NH3 toluene, reflux n-Bu a = Proton transfer d = Radical chain addition g= E2 Elimination b = Lewis acid/base e = Electrophilic addition h = Sy1 Nucleophilic substitution c = Radical chain substitution f=El Elimination i = SN2 Nucleophilic substitution Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - i for your answers. 1. 2.

Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - i for your answers.

Draw the curved arrows for the mechanism of the following acid-base reaction. NO ₂ + HF → HNO₂ + F Marvin JS :0: ——2=0 Edit drawing H :F: Help

Use the roadmap reactions to determine the steps reactions and the intermediate products for each synthesis. Help with 3&4 only!