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 a structural formula for the major product of the reaction shown. Cl2 CH3CH2CH=CHCH2CH3 H20 • Show product stereochemistry IF the reactant alkene has both carbons of the double bond within a ring. • Do not show stereochemistry in other cases. • If the reaction produces a racemic mixture, just draw one stereoisomer. opy aste ChemDoodle

Draw a structural formula for the product formed upon hydroboration/oxidation of the alkene below. CH3 OG 1 Use wedge and hash bonds ONLY for rings. Do not show stereochemistry in other cases. • If the reaction produces a racemic mixture, just draw one stereoisomer. ● 981 CH3 ***** // Q Y ? [F B

Choose reagents to convert 2-cyclohexenone to the following compounds.

Draw a structural formula for the major organic product of the following reaction: CH3 CH3 ● CH3 CH3 AAVIL + Br₂ Show product stereochemistry IF the reactant alkene has both carbons of the double bond within a ring. • Do not show stereochemistry in other cases. ● If enantiomers are formed, just draw one. CH₂Cl₂ Sn [F ? ChemDoodleⓇ

Draw a structural formula for the major product of the reaction shown. Br2 CHCH2CH3 H20 • Show product stereochemistry IF the reactant alkene has both carbons of the double bond within a ring. • Do not show stereochemistry in other cases. • If the reaction produces a racemic mixture, just draw one stereoisomer. ited ChemDoodle Previous Nex Save 11 étv МacBook Air 80 888 DII F3 F4 F5 F6 F7 F8 F9 F10 F11 $ & 4 5 7 8 { R Y U 0 P F G J K * 00 < (O

Following is a balanced equation for the allylic bromination of propene. CH2==CHCH3 + Br2 h CH2==CHCH2Br + HBr (a) Calculate the heat of reaction, H 0, for this conversion. (b) Propose a pair of chain propagation steps and show that they add up to the observed stoichiometry. (c) Calculate the H 0 for each chain propagation step and show that they add up to the observed H 0 for the overall reaction.

What is the major monobromination product of the following reaction? Disregard stereoisomers. What is the anticipated percent yield of the major product (as a percentage of all the monobrominated products)?

Draw a structural formula for the major organic product of the following reaction: CH2C2 Br2 • Show product stereochemistry IF the reactant alkene has both carbons of the double bond within a ring. • Do not show stereochemistry in other cases. • If enantiomers are formed, just draw one. opy aste ChemDoodle Previous MAR étv P 30 MacBook Air DD 80 888 F9 F10 F11 F7 F8 F3 F4 F5 F6 * $ % & 4 5 6. { Y * 00 R

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