Provide all requested information for the following transformation. Cl₂ CCl4 A. Complete arrow-formalism mechanism. B. Use a side-view to draw out the alkene HOMO + Cl2 LUMO. In a separate picture draw the alkene LUMO and Cl 2 HOMO. C. Indicate how many configurations are formed (and name them with R and/or S).

1. Provide the major product(s) for the following reactions. a. b. Br AlBr3 AICI3

6. Used curved arrows to demonstrate mechanisms behind given transformations. Show lone pairs where needed. A. B. C. Br Å Br + Lo Br solo H 05

8. a. Assign E or Z configurations to each alkene below. H₂C Br CH3 CH₂CH3 b. CH3 CN CH₂CH₂OH

Identify the correct structures in each step of the reaction sequence shown. 1) NaOCH2CH3 CH3CH,OH 1) Og CH CH,OH H,Cro. B C. 2) H30+ 2) (CH3),S H+ OH- 4. OEt 8. OEt OEt EtO. 9 OEt Eto A [Choose ] B [Choose] C [Choose ] D [ Choose ]

2 2. Show an alkyl bromide and some nucleophile that you could use to make the following by SN2 (not SN1). a. b. functional alkane A to alkene C. can't be accomplished in a single

2. Draw each reaction entirely using line structures and follow the instructions below. Give the structure of the reactant, reagent, or product omitted from each of the following reactions. CI ?M X X -=- CH₂CH₂CH₂C=CH CH₂CH₂CH₂C=CH CH₂C=CCH₂CH₂ 2 NINH, 2. CH₂CH₂Br HC1(1 mol) S CH₂CH₂CH₂CCH, (E)-2-pentene (CH₂)₂CHC=CCH₂CH₂ r

a) What is/are the major product(s) of this reaction? b) Which reagents best accomplish this transformation?

3. Draw all products for the following reactions. For your products, write whether the nucleophile added to the Re face or Si face of the starting material. a. HO b. 1) LIAIH 2) H™ 1) CH3CH2Li 2) H+ c) Determine whether the nucleophile added to the Re face or Si face of benzaldehyde.

Draw the major product from this reaction. Use wedge and dash bonds to indicate relative stereochemistry where appropriate. Ignore acid byproduct. 1. Br2, H₂O 2. NaOH Drawing Version: 1.177.0+ production