+ HCI CI Br + HBr

The following reaction can produce two products. The first of thes contains ONE double bond. What is the structure of this material?

Curved arrows are used to illustrate the flow of electrons. Follow the arrows and draw the intermediate and product in this reaction. Include all lone pairs. Ignore stereochemistry. Ignore inorganic byproducts. :O: H3C-MgBr Draw Intermediate H3O+ Draw Product Draw Tetrahedral Intermediate :0: CH3 H3C-MgBr Q

3) Draw the structures of the major organic product(s) for the following reactions. HI in CH₂Cl₂ 3 excess Cl₂ in H₂O H₂SO4 in H₂O (Two products) Br-Cl in THF 1) BH3 2) alkaline H₂O₂ OSO4 + HOOH

Provide stepwise synthesis show all reagents need and intermediates formed along the way

Please explain step by

When 2-iodo-1,4-dimethylcyclohexane is heated in acetic acid, CH3COOH, a mixture of substitution and elimination products is obtained. Provide structures for all possible products, writing [not drawing] the name of the mechanism by which each one is formed.

6) 25pts. Draw the structure of the major alkene product (or products) formed by treatment of each of the following haloalkanes with sodium ethoxide in ethanol. Assume the mechanism is E2 elimination. t-BuO K t-BUOH Br CH3 Eto Na F ETOH CH2CH3 CI H- Eto Na -CH2CH3 ELOH H- ČH3 Br Eto Na ELOH CH3 CI, H Eto Na CH2CH3 H3C H D ELOH

• Same reagents as acid-catalyzed dehydration, except starting with a instead of an alcohol. • Same as the general mechanism hydrohalogenation, except with . Remember that EVERY acid-cat. mechanism begins with General Reaction: EXAMPLE: Provide H₂O H₂SO4 EXAMPLE: Provide the mechanism for the following addition reaction. H₂O H₂SO4 OH WH H₂O H₂SO4 as the nucleophile and ends with do PRACTICE: Provide the mechanism and predict the product of the following reaction. MAXO

A common alkene starting material is shown below. Predict the major product for each reaction. Ignore any inorganic byproducts.