Select the final product for the following reaction sequence. OD 1. Mg, ether 2. D₂0

11. Draw the structure for the molecule that would yield the products shown below under the indicated reaction conditions. Br 1 molar eq HBr -78 °C 1 molar eq HBr 50 °C Br

What are the major products of these reactions?

Give starting materials, reagents, and conditions that will produce each product.

Predict each product for the following multistep reaction. If ortho/para products are both formed, use the para product in the next reaction. 46. Predict each product for the following multistep reaction. If ortho/para products are both formed, use the para product in the next reaction. Br2 FeBr3 HNO3 A H2SO4 B Fe C HCI NaNO3 CuCN D E H₂O F G

7. The reaction of methoxide anion with bromoethane to yield the ether ethyl methyl ether and the bromide anon (Br-) is an excellent example of a general reaction type called Sy2 (substitution nucleophilic bimolecular): CH,0+ CH,СH-Br a CH3-0-CH,СH; + Br- a. Change in enthalpy is -103 kJ/mol; the change in entropy is + 0.025 kJ/mol-K. Calculate DG at 300K. b. Is the reaction endergonic or exergonic? c. Is the reaction endothermic or exothermic? d. Use curved arrows to show the complete mechanism. Reaction of 2-methyl-1-butene with H-Cl could yield TWO alkyl chloride products. Draw and name 8. them.

12. Draw the structure of the major organic product(s) for the following reactions and name the reaction. CH3 N-CH3 CI CH3 heat a. (name of reaction) 0- N-CH3 CI CH3 b. (name of reaction) -NH2 + CH3CH2Cl c. (name of reaction) heat NaOH 2 H d. name of reaction H3C e. name of reaction CH3 1. EtQ Na+ 2. H2O, HCI

Specify both the alcohol starting material and the reagents you would use in each step in a synthesis of the compound shown. If the synthesis requires only two steps enter "none" for step 3. r Alcohol Starting Materials 1. methanol 2. ethanol 3. 1-propanol 4. 2-propanol 5. cyclohexanol Reagents available a. LiAlH₁ f. PBr3 b. H₂SO4 c. HCI d. HBr i. CH3 MgBr; then H3O+ e. SOC1₂ j. CH3 CH₂ MgBr; then H3O+ g. CrO3, H₂ SO4, H₂O h. NaH k. CH3 CH₂ CH₂ MgBr; then H3O+ I. C6H5 MgBr (phenylmagnesium bromide); then H3O+ m. (CH3)2 CHMgBr: then H3O+t n. Dess-Martin periodinane (DMP) Write the number/letters of the alchol/reagents in the boxes below. Alcohol starting material Reagent for step 1 Reagent for step 2 Reagent for step 3