Which product (or products) would you expect to obtain from each of the following reactions? In each part give the mechanism (SN1, SN2, E1, or E2) by which each product is formed and predict the relative amount of each product (i.e., would the product be the only product, the major product, a minor product, etc.?). H3C H3C CH 3 H3C H3C Br CH3 H3C Br H3C Br Br EtO EtOH, 50 °C t-BuOK t-BuOH, 50 °C MeO MeOH, 50 °C t-BuOK t-BuOH, 50 °C

Identify the major product of the following reaction sequence. 1) [H*], H₂NNH2, (-H₂O) 2) KOH/H₂O, heat HO₂C HO₂C HO CO,H OH OH There is no reaction under these conditions or the correct product is not listed here.

Write the major product of each reaction and what kind of mechanism it is: sn1, sn2, e1, e2.

Be sure to answer all parts. What is the major product formed when the following alkyl halide is treated with each of the following reagents: [1] NaOCOCH3; [2] NaOCH3; [3] KOC(CH3)3? If it is not possible to predict the major product, identify the products in the mixture and the mechanism by which each is formed. Part 1: It is possible to predict the major product for: NaOCOCH3 NaOCH3 KOC(CH3)3 none of the reagents Part 2 out of 2 Major product with [1] NaOCOCH3: Major product with [2] NaOCH3: Major product with [3] KOC(CH3)3: Check my work edit structure ... draw structure ... draw structure ... Next part Hint ?

Which product (or products) would you expect to obtain from each of the following reactions? In each part give the mechanism (SN1, SN2, E1, or E2) by which each product is formed and predict the relative amount of each product (i.e., would the product be the only product, the major product, a minor product, etc.?)

2) reaction sequences to carry out those transformations. Draw the expected product of each step proposed. Substantial partial credit can be obtained for incomplete or incorrect answers. You may present your solutions on the following blank page if you need the the following reaction transformations, and propose room. H3C CH, H3C CH3 of HN- -NH HO,C Co,H но H,C CH3 CEN OCH3 OCH3

CS41 10.) Chapter 7: E2 SNI + EI SN1+ E1 Mechanisms. Using correct mechanistic arrows, provide the step-by-step mechanism that demonstrates how the following reactions proceed to afford both substitution and elimination products via SN1 and E1. You do not need to show stereochemistry while providing the mechanism, but show correct stereochemistry in the final product(s). If there is more than one product feel free to write +E or +D as appropriate (or just write your products). C341 Br CH3NH2 CH3CH2OH CH₂OH Br CH3CH₂OH A Page 5 of Chapter 7: E2 SNI + E1

Predict the all the products of the following reactions. Be sure to consider all reactions (SN1, SN2, E1, E2). 1-bromohexane + sodium ethoxide in ethanol (two products) S-2-chlorohexane +  NaOCH₃ in methanol. There are three elimination products and one substitution product. 2-chloro-2-methylbutane +  NaOCH₂CH₃ in ethanol 2-chloro-2-methylbutane heated in ethanol 1-bromo-1-methylcyclopentane +  NaOEt in ethanol

Draw the major organic product of the reaction shown below. -OH 3) K₂Cr₂O7 H₂SO4, H₂O You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. Ⓒ Sn [F ? ChemDoodleⓇ 6a

10) What is the major product of the following reactions? CH3 + HCI H₂O H* ? CH3CO3 H HBr 11) Which is more highly regioselective the addition of HCl to methylenecyclohexane or to 1- methylcyclohexene? Explain. What product(s) is/are formed when the following compound react with ozone and then with dimethyl sulfide (i.e. ozonolysis)? a) b)