H H3C N. N. H3C. N. AICI 3 N-phenylacetamide

6. Provide the full mechanism for the Friedel-Crafts Acylation reaction in the first step of the scheme in #5. De AICI₂

Cinnamoyl chloride (C9H7CIOO) can be prepared by the two-step sequence shown below. Reaction 1: C7H60 + CAH6O3 C9H8O2 + C2H402 Reaction 2: C9H&O2 + SOC2 → C9H7oci + sO2 + HCI CH60 C4H6O3 C9H8O2 C2H402 SOCI2 C9H,Oci SO2 HCI Molar masses 106.12 102.09 148.16 60.05 118.96 166.60 64.07 36.46 (in g mol-1) What is the percent atom economy for the synthesis of cinnamoyl chloride? Enter an answer accurate to three significant figures. Number

1. Draw 2-methylpropanoic acid + thionyl chloride/pyridine catalysis + heat = ibuprofen intermediate  C4H6OCI is the answer for the first intermediate  (this one I already have it) 2. Draw ibuprofen intermediate 1 + benzene + AlCl3 + heat = ibuprofen intermediate 2. 3. Draw ibuprofen intermediate 2 + hydrazine = ibuprofen intermediate 3. 4. Draw ibuprofen intermediate 3 + KOH + heat = ibuprofen intermediate 4. 5. Draw ibuprofen intermediate 4 + ethanoyl chloride + AlCl3 + heat = ibuprofen intermediate 5. 6. Draw ibuprofen intermediate 5 + NaBH4 + hydronium workup = ibuprofen intermediate 6. (this one I have it already) 7. Draw ibuprofen intermediate 6 + HBr = ibuprofen intermediate 7.   (this one i have it already)8. Draw ibuprofen intermediate 7 + Mg = ibuprofen intermediate 8. 9. Draw ibuprofen intermediate 8 + CO2 = ibuprofen intermediate 9. 10. this is the ibuprofen (i already have it)

2. Complete the following reactions and provide the reaction mechanism: Br2, FeBr3 H*

Assuming that each of the following alkyl bromides undergoes an S№1 reaction, which substrate's carbocation intermediate is most likely to undergoes a rearrangement? (......Hint: Remember that a 1,2-shift can involve a shift of -H or -R). = Select one: A. II B. III C. IV D. I Br Br IV Br Br €

The two reactants shown below are combined to bring about a nucleophilic substitution reaction. [Review Topics) [References) -F Nal d. F- g. HI e. I f. HF h. Na* i. none Which letter designates the electrophilic carbon at which substitution occurs? (If no reaction occurs enter the letter corresponding to "none.") Which letter corresponds to the leaving group? Which letter designates the nucleophile?

Furfuryl ethyl ether (FEE) was identified as a component that forms in aged beer, giving it a solvent-like taste U. Agric. Food Chem, 2004, 52, 1661) This ether can be formed from furfuryl alcohol (FALC, by either S,1 or S2 mechanisms. CH,CH,OH OCH,CH, furtury alcohol (prolonatec) furfuryl ethyl ether FEE) Draw a reasonable mechanism of the SN1 formation of FEE. Explain why it is possible for FALC to underga a SNI reaction, even though it would have to form a primary carbocation

Draw the major organic product from the reaction sequence. Select Draw Rings More Erase H. 1. Excess CH3MGBR 2. H3O* 3. NaH, THF 4. CH;CH2CH,Br

8) Draw the mechanism and major product of the following dehydration (E₁) reaction OH Catalytic amount of H3O+ (no solvent). 75 °C