Draw the structures of the products, showing stereochemistry where relevant. 3. a) 1-methylcyclohexene HBr Br2 1-methylcyclohexene Br2 1-methylcyclohexene H2O 4. When bromine adds to the double bond in cyclohexene, the resulting dibromide is trans. This stereochemistry is due to: a) The intermediate bromonium ion d) Markovnikov's rule b) the intermediate carbocation d) IUPAC rules

Draw a structural formula for the major organic product of the reaction shown below. S. 10 + 2 + ether -CuLi H3O • You do not have to consider stereochemistry. √n [F ? ChemDoodle

The reaction of the following alkyl halide with water yields an alcohol product. Which statement below is the best description of the stereochemistry of the product? H₂C CH₂CH₂ CH₂CHICH₂ CI H₂O ethanol O The product has (S) stereochemistry. O The product has (R) stereochemistry. O The product is a mixture of (R) and (S) with slightly more (R) than (S). O The product is a mixture of (R) and (S) with slightly more (S) than (R). The product is neither (R) nor (S); it does not have a chirality center.

The following compound reacts with NaOMe in an SN2 reaction. Draw the transition state and the final product of the reaction and use the transition state geometry to explain the stereochemical outcome of the reaction. What is the side-reaction that might occur and what would be the major product of that reaction? Br NaOMe ČH3

1. Provide a name or a structure for each of the following compounds include stereochemistry as appropriate میر مهاله H OH Br

Provide the major product(s) of each reaction below. Show the stereochemistry of each stereocenter (for example, by using wedge-dash structures for chirality centers and clear bond angles for alkenes). For enantiomers, you only need to draw one of the enantiomers. Br2, H₂O 1) 03 2) MeSMe H₂, Pd/C HgSO4 H₂SO4 H₂O 1) BH3 2) NaOH, H₂O2 H₂O 1) 9-BBN 2) NaOH, H₂O2 H₂O

O which alkene is favored in a product mixture ations/anions/radicals the stability of carbocation intermediates O the stereochemistry of reaction intermediates/transition states Question 7 Which mechanism(s) feature(s) a single transition state with no intermediate? SN2 O SN1 and SN2 O SN1 O E2 and SN2 O E2 Question 8 A hydrogen and the leaving group have to be antiperiplanar in which reaction? 17

What is the possible products for following compound with one equivalent of HBr? 3,4 dimethyl-hepta-2,4-diene a) 3 bromo-4,5-dimethyl hepta-3-ene and 4- bromo-3,4-dimethyl hepta-2- ene b) 3 bromo-3,4-dimethyl hepta-3-ene and 4- bromo-3,4-dimethyl hepta-3- ene c) 3 bromo-4,5-dimethyl hepta-2-ene and 3- bromo-3,4-dimethyl hepta-2- ene d) 3 bromo-4,5-dimethyl hepta-3-ene and 4- bromo-3,4-dimethyl hepta-3- ene e) 3 bromo-4,5-dimethyl hepta-3-ene and 2- bromo-3,4-dimethyl hepta-2- ene O a. e O b. b O c.d O d. c O e. a

Draw the product(s) you would expect from the following reaction. CH3 H₂C CH3 CH₂ + H₂C=CHCCH3 heat • 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 give one.

Draw the product (s) of the following reaction. If the formation of one product is preferred over the other stereo specifically or stereoselectively, then draw Newman projections to show why. Determine the stereochemistry of the product (s).