Give complete reaction equations that show all intermediates, reagents and product if (R) -3- chloro- cyclopentene is used in the DEM synthesis. Show the stereochemistry of the product.

what is the structure of the substitution product in the following reaction and consider stereochemistry in deciding your product?

Alkenes can be converted to alcohols by hydroboration-oxidation. (a) Draw the structure of the alcohol or alcohols formed in the reaction sequence. Clearly indicate stereochemistry by drawing a wedged bond, a dashed bond and two O Hint in-plane bonds per each chiral carbon. Draw hydrogen atoms that are connected to wedge-and-dash bonds.(b) Characterize the product or products of the reactions. The first step of the reaction, hydroboration, involves addition of BH, to the double bond, with -BH, attached to one carbon and hydrogen Be sure to draw hydrogens on oxygen, where applicable. attached to the other. Consider both Rings the regioselectivity and the Select Draw More Erase stereochemistry of this addition. H Diborane, B,H,, is a source of borane, BH,, and can be used 1. B2H6, interchangeably. Diglyme is a solvent. diglyme 2. H2О2, НО", The product or products of the reaction are characterized as being O S. O racemic. O achiral. O R,S (and/or S,R). O R. O S,S. O R.R. O diastereomers.

Draw the alkene that would react with the reagent given to account for the product formed. ? + H₂O ● 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 draw one. 8 H₂SO4 // CH3 CH3CHCCH3 OH CH3 ? [F Previous Email Instruct

How would you synthesize the following compounds from benzene using reagents from the table? Reagents Cl2 1. NaOH / H2O 2. Hзо" CH3CI / AICI3 i a e CH3CI NBS / (PhCO2 b f Br2 / FeBr3 Cl2 / FeCl3 1. CO2 2. H3O* HNO3 / H2SO4 g k d NaCN KMNO4 / H3O* Mg / dry ether a) Phenylacetic acid, C¿H3CH2CO,H b) p-Methylbenzoic acid (p-toluic acid) Submit Answer Try Another Version 9 item attempts remaining

Provide the structure of the product(s) with stereochemisty if appropriate. If multiple products indicate major product or if products are formed in equal amounts. If there is no reaction expected explain why. (a) OH HIO4 (the protecting group is remained) CHO H HOH2C OH (b) CHO -ОН NaCN # HO -H H -OH CH₂OH (c) CHO HO- -H HO -H NH₂OH 張一 H -OH H -OH CH₂OH i) Ba(OH)2 ii) MeOH, H₂SO4 NaOAc Ac₂0 NaOMe MeOH

МСРВА Alkenes are oxidized to give epoxides on treatment with a peroxyacid, RCO3H, such as metachloroperoxybenzoic acid (MCPBA). Peroxyacids transfer an oxygen atom to the alkene with syn stereochemistry, i.e. both C-O bonds form on the same face of the double bond, through a single step mechanism without intermediates. The oxygen atom farthest from the carbonyl group is the one transferred. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H .CI .CI HO

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.

a) H₂ Pd C-C -H and -H + A-B For the following reagents, indicate the following: a) what is added accross the double bond; b) is the addition stereoselective/stereospecific? If yes, do A and B add syn or anti?; c) draw the product, with relevant stereochemistry, when the reagent system shown is reacted with 1-methylcyclopentene. The answer to the first reagent system is shown below. (i) b) yes, syn addition | | -C-C- (achiral, stereochem. not observable) | I A B (ii) a) 1) 9-BBN 2) H₂O2, NaOH(aq) b)

Draw the structure of the expected organic product(s) formed in the following reactions including correct stereochemistry. If the product is racemic write both isomers or write racemic. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state 'No Reaction'