Experiment 8_ Dihydroxylation with KMnO4 (1)

Consider the following reaction. O + 0 CHBr3 Draw the major organic product formed in this reaction. 81 + [**** (CH3)3CO¹K+ • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Include H atoms at chiral centers only. • Show stereochemistry in a meso compound. If the reaction produces a racemic mixture, just draw one stereoisomer. - √n [F] ?

Draw the structure of the alkene with the molecular formula CH10 that reacts with Br, to give this compound. CH3 Br Br • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. opyste ot pt pt pt pt

Draw a structural formula for the substitution product of the reaction shown below. ● H3C- ● H3C H Br + Na OCCH3 DMF • Use the wedge/hash bond tools to indicate stereochemistry where it exists. If more than one stereoisomer of product is formed, draw both. Separate multiple products using the + sign from the drop-down menu. Products that are initially formed as ions should be drawn in their neutral forms. DMF = dimethylformamide

Shown below is a carbocation intermediate in an electrophilic addition reaction of HCl with an alkene. For the conformation shown, select each hydrogen whose bond to carbon is aligned for effective hyperconjugation with the vacant p orbital on the positively charged carbon. Each adjacent carbon will have only one C-H bond so aligned. • Gray = C; white = H; red = 0; blue = N; dark green = Cl; brown =Br; light green =F; purple = I; yellow = S; orange = P. • Double click to select atoms. • You can zoom in and out using the mouse scroll wheel (or pinch to zoom on touch screens).

Draw the structure of the major organic product of the reaction below. CH3 Zn(Cu) CH3CHCH=CH2 + CH212 Use the wedge/hash bond tools to indicate stereochemistry where it exists. Show stereochemistry in a meso compound. • If the reaction produces a racemic mixture, just draw one stereoisomer. opy aste ChemDoodle

Draw a structural formula for the substitution product of the reaction shown below. H CH3 Br 0 OCH2CH3 + N-H • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • If more than one stereoisomer of product is formed, draw both. Separate multiple products using the + sign from the drop-down menu. Products that are initially formed as ions should be drawn in their neutral forms. O ▼ 0 Θ ?

Draw the structure of the major organic product of the reaction below. ● ● =CH₂ + CHCI3 KOH Use the wedge/hash bond tools to indicate stereochemistry where it exists. Show stereochemistry in a meso compound. If the reaction produces a racemic mixture, just draw one stereoisomer. ? ChemDoodleⓇ

Schlapbach and Hoffmann used a stereoelectronic effect to control the stereochemistry of the reaction below. Draw the structure of the transition states for competing reactions to explain the origin of stereoselectivity. lag X = CI, OR, N(Me)SO₂R R H + Me R OH Me X

A 1.52 M solution of (R)-2-butanol is mixed with an equal volume of a 0.760 M solution of racemic 2-butanol, and the resulting solution is analyzed in a sample container that is 1 dm long. What observed rotation is expected? The specific rotation of (R)-2-butanol is -13.9 degrees mL g-¹ dm¯¹. α = deg

Draw the structure of the major organic product of the reaction below. CH3 CH₂CHCH₂CH₂CH=CH₂ + CHC13 KOH • Use the wedge/hash bond tools to indicate stereochemistry where it exists. Show stereochemistry in a meso compound. If the reaction produces a racemic mixture, just draw one stereoisomer.

Draw the organic product of the reaction below. Show stereochemistry when relevant. If the product exists as a pair of enantiomers, draw only one. Ä + T 1. LIAIH 4 2. H₂O 2 X Ś è Click and drag to start drawing a structure. 8 00. Ar ▶

4-tert-butylcyclohexanol

Draw the structure of the major organic product of the reaction below. ● + CHCI3 MILL KOH Use the wedge/hash bond tools to indicate stereochemistry where it exists. Show stereochemistry in a meso compound. If the reaction produces a racemic mixture, just draw one stereoisomer. ▼ n [F ? ChemDoodleⓇ

2. Draw all stereoisomers for the following molecules; indicate the stereochemical relationships for all possible pairs. Br HO Br ОН но H3C Br (G)

Draw a structural formula for the major organic product of the reaction shown below. + ether H3O CH3CH2CH2CH=CCCH2CH3 + (CH3)2CuLi CI • You do not have to consider stereochemistry. √n [F ? Chem Doodle Ⓡ

The reaction below involves 2-chloropentane reacting with water. The product of this reaction is 2-pentanol. What would be the stereochemical result of the product? CH3 OH c CH;CH2CH3 H20 H. a. 100% R b. 100% S O C. ~50% R, ~50% S

16. Ignoring stereochemistry, what is the enthalpy difference of the second propagation step of 1,3,5- trimethylcyclohexane, chlorine, and light going to the major mono-chlorinated product? + Bond Disassociation Energies (kcal/mole) Selectivity Ratios C-H C-F C-CI C-Br X-X H-X 1º 2° 3° 1༠ 98 107 81 68 F 38 136 F 1 1.2 1.4 2° 95 106 80 68 CI 58 103 Cl 1 4 5 3° 91 106 79 65 Br 46 88 Br 1 80 1700 a. -8 b. -22 c. -30 d. -58 e. not a.-d.

Draw the structure of the major organic product of the reaction below. CH=CH₂ ● ● + CH₂1₂ Zn(Cu) ether Use the wedge/hash bond tools to indicate stereochemistry where it exists. Show stereochemistry in a meso compound. If the reaction produces a racemic mixture, just draw one stereoisomer. #[ ] در ? ChemDoodleⓇ

parts a and b

The Diels-Alder reaction between butadiene and dimethyl maleate yields a ring structure, as shown in the product. Complete the structure by drawing any missing bonds and indicating the stereochemistry of the new stereocenters. Select Draw Rings More Erase H 160 °C 24h H

N,N-diethyl-m-toluamide (DEET) is the active ingredient in many insect repellent preparations. Following is one of the steps in its synthesis. In the box below draw the structure of the product of this reaction. MgBr H3C 0 ▾ + 1. CO₂ 2. H3O+ • You do not have to consider stereochemistry. • 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. • Draw the Grignard reagent as a covalent magnesium bromide. n [ ]# product ChemDoodleⓇ 28

Draw a structural formula for the substitution product of the reaction shown below. Br Na ОCH3 H3C CH3OH • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • If more than one stereoisomer of product is formed, draw both. • Separate multiple products using the + sign from the drop-down menu. • Products that are initially formed as ions should be drawn in their neutral forms. C opy aste ChemDoodle'

Draw the structure of the major organic product of the reaction below. CH=CH2 Zn(Cu) + CH2l2 ether •Use the wedge/hash bond tools to indicate stereochemistry where it exists. •Show stereochemistry in a meso compound. • If the reaction produces a racemic mixture, just draw one stereoisomer.

4. Find the R and S configuration in the following compounds. H OCH 3 HOCH 2 CO₂H 5. Draw the product of the following reaction? Br OC(CH3)3 6. Find the R and S configuration and name the following compounds. H OH H H3C 7. Draw the product of the following reaction explain if there is any stereochemistry. Br NaOH -HBr

Name (including E/Z stereochemistry) the five alkenes that can produce 3-bromo-3-methylhexane on reaction with HBr.  Draw the skeletal structure of each molecule.