Strain Energies for Monosubstituted Cyclohexanes Substituent kJ/mol Substituent kJ/mol -CN, cyano -F -I -CECH, ethynyl 0.85 -CI -Br -OH -C6H5 0.4 Br 0.5 NC 0.95 1.1 1.2 1.95 6.3 -NH₂ Br -COOH CN 7° 2.95 2.95 -CH=CH₂ -CH3 -CH₂CH3 -CH(CH3)2 4.5 -C(CH3)3 Click on the following structures that represent the most stable conformation of trans-1-bromo-3-cyanocyclohexane. 3.55 3.64 3.65 10.5 Br CN CN

Which structure corresponds to the name 4-chloro-2-ethyl-1-methylcycloheptane? CH3 CH3 OI 0 0 0 0 I 11 O IV OV CI -CH3 H3C IV -CH3 CI CH 3 CI CH3 CH3 M III CH3 CH3

Using the table of bond energies estimate the heat of combustion of one mole of 2,4-dimethyl-1,3-pentadiene.

Treating cyclohexene with Br₂ yields trans-1,2-dibromocyclohexane. Justify why the cis isomer is not formed. Br Br2 Br

Esc smooth 0 CH₂- Ph -CH-CH3 (3) (CH3)3C-C=C—CH(CH3)CH₂CH3 CH3 5c CH₂-C=C-C-OH T CH₂CH3 CH3 C C-CH₂CH3 53-methyloct-4-yne H₂C CH3 H C=C-CH₂CH₂ CH3 -CBr₂ C=C-CH3 CH,–C=C–CH3 Ph-C=C-H (CH₂)₂C-C=C—CH(CH₂) CH₂CH3 Chapter 9 Alkynes Quiz 2 1. Name each molecule. 2. Use the molecules in the reactions 1 through 9 highlighted in red to determine the product. 3. Draw the line/angle or skeletal structure of eachmolecule. 4. Use the alkyne below to predict the products 1- 9.

Name the following cycloalkane with alkyl groups C2H5 C2H5 キ H CH3 C-H Н—с С —н CI- CH3 H CH3 CH3 CH3 CH3

contains a tertiary carbon. OH-C=C-CH3 Obromocyclohexane CH2=CH-CH=CH-CH=CH2 C6H5-CH2-Br O2-iodopentane 0000

Which of the following options correctly describes the reaction shown (use the data provided to help answer the question)? + H-CI Bond dissociation energies secondary C-Cl: 81 kcal/mol secondary C-H: 95 kcal/mol alkene C=C pi bond: 65 kcal/mol H-CI: 103 kcal/mol secondary C-secondary C sigma bond: 83 kcal/mol The reaction is an addition and is exothermic by 8 kcal/mol The reaction is a substitution and is endothermic by 8 kcal/mol The reaction is a substitution and is exothermic by 8 kcal/mol The reaction is an addition and is endothermic by 8 kcal/mol

5. a-G a- Convert the following Newman projection into the bond line structural formula. Must use stereobonds to indicate the orientation of the groups. H3CO CN b- Draw the anti, gauche, and eclipsed conformations of the following molecule using Newman projection. H H H H c- i. Which cyclopropane molecule has the highest torsional strain? ii. Which cyclopropane molecule has the lowest torsional strain? C b a

What is the IUPAC name for this molecule?