18) Which one of the following reaction steps work best to carry out the transformation shown below? 1) BH, THE PCC A) 2) H2O2, NaOH CH2Cl2 H2O, H₂SO (cat.) PCC B) B) CH2Cl2 1) BH3, THF HIO4 C) 2) H2O2, NaOH D) OsO K2Cr2O7, H₂SO₁ (CH3)3COOH, OH H₂O H

Rank the following molecules relative reactivity from slowest to fastest under SN1. Br A [Select] [Select] Br B Br [Select] [Select] C Br Hy D H V

Decide which of the following molecules these statements belong to. Each molecule is only used as answer once. Br A B Br C Br D This molecule has the highest reaction rate of [Choose ] all in an SN2 reaction. [Choose ] This molecule has the highest reaction rate in an D SN1 reaction. A This molecule can neither react by an SN1 nor an SN2 mechanism. E B This molecule can react by an SN1, E1 or E2 mechanism but will never react by an SN2 mechanism. C F This moelcule can react my an SN2 or E2 mechanism but will not react by an SN1 or E1 mechanism. [Choose] This molecule reacts rapidly by either an SN1 or [Choose ] an SN2 mechanism. له Br Br E F Br

9. Complete Reactions. Provide only the major product for E2&SN2 reactions. E1/SN1 provide all possible products. NaOH Br provide mechanism CI Provide mechanism + CI NaOCH 3 KCN

Rank the following molecules in order of increasing relative rate of SN1 reaction with methanol, CH3OH (slowest to fastest reacting). Br Br CH3-Br 1 X X X Br Br 2 5 4 3 C) 5<4<3<2<1 A) 1<2<4<3<5 D) 4 <2<3<5<1 B) 5 < 1<2<4<3 E) 1<2<5<3 <4

2. Draw the structures and explain why CH3CH₂O and CH3CO₂ are good nucleophiles but CH3SO3, water, and alcohols (R-OH) are poor nucleophiles. Propose a 'cutoff' for the amount of negative charge needed to be a good nucleophile. CH3CH₂O CH3CO₂ CH3SO3 H₂O CH₂OH

Use the E2 mechanism to explain why when I is mixed with sodium ethoxide (NaOEt) in ethanol, the major product is III, but when II is mixed with sodium ethoxide in ethanol, the major product is IV. H3C CH3 H3C CH3 ..CI CI CH3 I CH3 || H3C. CH3 H3C CH3 E ||| CH3 CH3 IV SAN

Your task is to convert 2-bromobutane to 1-butene in highest yield. Which reagents would you use? O KOH/H2O O KOH/CH,OH O CH3CH2ONA/CH3CH2OH O CH3ONA/CH3OH O (CH3)3COK/(CH3)3COH

DRAW a stepwise reaction mechanism for this reaction. NO₂ -N3 C c 03, NaHCO3, CH2C12/MeOH. then Ac20, Et3N NO₂

HO. Provide a detailed, step-by-step mechanism for the reaction shown below. Br₂ Br HBr