TOMA is a conformational stereoisomer of trans-1,2-dimethylcyclohexane. It is converted to conformer ATOM through ring-flip. ring-flip CH3 CH3 АТОМ ΤΟΜΑ a. Draw the structure of the conformer ATOM in sawhorse and Newman projections b. Calculate the strain energies of ATOM and TOMA given the following energy values. Show necessary solutions. ENERGY ENERGY INTERACTION INTERACTION INTERACTION ENERGY (kcal/mol) (kcal/mol) (kcal/mol) 1,3-diaxial gauche CH3- eclipsed CH3- 1.0 3.0 0.9 CH3 CH3 (one CH3-H) eclipsed CH3- 2.0 CI 2.0 1,3-diaxial gauche CI - Cl 0.25 |(one Cl-H) 4.0 gauche CH3-CI 1.4 eclipsed CI-CI c. Which is more stable between the two conformers?

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TOMA is a conformational stereoisomer of trans-1,2-dimethylcyclohexane. It is converted to
conformer ATOM through ring-flip.
ring-flip
CH3
CH3
АТОМ
ТОМА
a. Draw the structure of the conformer ATOM in sawhorse and Newman projections
b. Calculate the strain energies of ATOM and TOMA given the following energy values. Show
necessary solutions.
ENERGY
ENERGY
INTERACTION
INTERACTION
ENERGY (kcal/mol)
INTERACTION
(kcal/mol)
(kcal/mol)
1,3-diaxial
gauche CH3-
CH3
eclipsed CH3-
1.0
CH3
3.0
0.9
(one CH3-H)
eclipsed CH3-
2.0
CI
2.0
1,3-diaxial
gauche CI - CI
0.25
(one Cl-H)
gauche CH3-Cl
1.4 eclipsed Cl-CI
4.0
c. Which is more stable between the two conformers?
Transcribed Image Text:TOMA is a conformational stereoisomer of trans-1,2-dimethylcyclohexane. It is converted to conformer ATOM through ring-flip. ring-flip CH3 CH3 АТОМ ТОМА a. Draw the structure of the conformer ATOM in sawhorse and Newman projections b. Calculate the strain energies of ATOM and TOMA given the following energy values. Show necessary solutions. ENERGY ENERGY INTERACTION INTERACTION ENERGY (kcal/mol) INTERACTION (kcal/mol) (kcal/mol) 1,3-diaxial gauche CH3- CH3 eclipsed CH3- 1.0 CH3 3.0 0.9 (one CH3-H) eclipsed CH3- 2.0 CI 2.0 1,3-diaxial gauche CI - CI 0.25 (one Cl-H) gauche CH3-Cl 1.4 eclipsed Cl-CI 4.0 c. Which is more stable between the two conformers?
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