EtOH 1. + NaQEt [Review Topics] [References] NaCl HOEL 2. Br Acetone + Nal a = Proton transfer b = Lewis acid/base C c = Radical chain substitution d = Electrophilic addition e E1 Elimination f = E2 Elimination + NaBr g= SN1 Nucleophilic substitution h = 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.

For the following multi-step reaction, read the curved arrows and identify the sequence of arrow-pushing patterns where 1 is the loss of the leaving group, 2 is the nucleophilic attach, 3 is the proton transfer and 4 is rearrangement. :0: H. `NH2 `NH2 H но: NH HO:HN- H,0 HN

Heck reactions take place with alkynes as well as alkenes. The following conversion involves an intramolecular Heck reaction followed by an intermolecular Heck. Work out the reaction sequence on a separate sheet of paper, and then draw the structure of the palladium-containing intermediate A. 1% mol Pd(OAc)₂2 CO₂Me 4% mol Ph P CH₂CN A (1 ring) C (2 rings) (2 rings) • Consider E/Z stereochemistry of alkenes. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • Use R1 to represent the palladium complex. The R group tool is located in the charges and lone pairs drop-down menu. 0- ✪ Sn [F MeO₂C

Fill in missing reactants/reagents/products for each case accordingly in correct order.

7) Provide the structure of the major organic product in the following reaction. HOT 7a) 7b) 7c) CH3 H3CO. H3CO. H3CO. CI. H. CN X· X- NC H 7d) H3CO CI CO₂CH3 A A A

Fill in the boxes with reagents or products and show the mechanism.

4. Fill in the boxes with the reactants, reagents, or products for each reaction. Underneath each reaction, propose a complete mechanism for the transformation. Ph NH₂ B & B & (there is excess of all reagents) 1. CH₂l (excess) 2. Ag₂O 3. heat Br₂ NaOH 1. NaNHz 2. H3O+

1. MgBr 1. Dry ether OH 2. Hао 2. Br AIB 3 AIBra d = Electrophilic addition g = SN1 Nucleophilic a = Proton transfer substitution h = SN2 Nucleophilic b = Lewis acid/base e = El Elimination substitution c = Radical chain f= E2 Elimination 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. Submit Answer Retry Entire Group 8 more group attempts remaining

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) For each reaction below, provide the product and type (ketone/aldehyde/enol/enolate) of the reactant and the product. The equilibrium arrows are generic: a) Туре b) Туре c) Type d) Type OH ]}₁ OH H3O* catalyst H₂O H3O* catalyst H₂O OH catalyst H₂O OH catalyst H₂O Product Туре Product Type Product Type Product Type