Exam 4: Organic Compounds: Cycloalkanes and Their Stereochemistry

What is the energy difference between the two chair conformations of the following compound that is due to steric strain? cis-1-bromo-4-isopropylcyclohexane Assume the following 1,3-diaxial strains. Br: 1.0 kJ/mol CH(CH₃)₂: 4.6 kJ/mol

Substitution of which of the following groups on a cycloalkane would result in the greatest amount of steric strain?

(−)-Menthol is responsible for the characteristic flavor and taste of peppermint. The structure of (−)-menthol is shown below. Use this information to answer the following question. -Refer to instructions. On the chair template provided below, draw the two chair conformations that are in equilibrium for (−)-menthol.

For each pair of molecules below, circle the most stable. and

For each disubstituted cyclohexane below, draw its ring-flip isomer. Circle the most stable conformation and label the substituent groups as axial or equatorial. -Draw and label:

Label each pair of compounds below as: -Label: and

Which of the following cycloalkanes would be the most similar to its open chain counterpart?

Draw and name the seven constitutional isomers for cycloalkane, C₆H₁₂.

Refer to the structure below to answer the following question(s). -Refer to instructions. Which groups have a 1,3-diaxial interaction with each other?