A. Propane Measurements:C1–C2–C3 bond angle1.H–C2–H bond angle2.H–C1–C2 bond angle3.H–C1–H bond angle4.C–C bond length in propane5.B. 2,2-Dimethylbutane Measurements: Carbon numbering here refers to IUPAC numberings.C2–C3–C4 bond angle6.anti-C1–C2–C3 bond angle7.gauche-C1–C2–C3 bond angle8.C2–C3 bond length9.C. Butane Measurements:Strain energy—anti conformation10.C1–C2–C3 bond angle—anti11.H–C1–C2 bond angle—anti12.DAtA & AnALYSiS Molecular Modeling I 75C1–C2–C3–H dihedral angle—anti13.Strain energy—gauche conformation14.C1–C2–C3 bond angle—gauche15.C1–C2–C3–C4 dihedral angle—gauche16.C1–C4 H–H distance—gauche17.H–C1–C2–C3 dihedral angle—gauche18.PART II. BOND ROTATION IN BUTANE (STRUCTURES AND ENERGIES)Dihedral angle—eclipsed conformation19.Relative energy—eclipsed20.C1–C2–C3 bond angle—eclipsed21.C1–C4 H–H distance—eclipsed22.C2–C3 bond distance—eclipsed23.C1–C2 bond distance—eclipsed24.Dihedral angle—second eclipsed conformation25.Relative energy—second eclipsed26.C1–C2–C3 bond angle—second eclipsed27.C2–C3 bond distance—second eclipsed28.76WRITE-UPPART III. CONFORMATIONAL ANALYSIS OF SUBSTITUTED CYCLOHEXANESStrain energy—diaxial 1,2-dimethylcyclohexane29.Me–C–C–Me dihedral angle—diaxial30.Strain energy—diequatorial 1,2-dimethylcyclohexane31.Me–C–C–Me dihedral angle—diequatorial32.Strain energy—axial-equatorial 1,2-dimethylcyclohexane33.Me–C–C–Me dihedral angle— axial-equatorial34.PART IV. COMPARISON OF AXIAL AND EQUATORIAL STRAIN ENERGIES FOR TRIMETHYL-X SUBSTITUENTS A. t-Butylcyclohexane:Strain energy—axial t-butylcyclohexane35.H–C–C–CMe3 dihedral angle— axial t-butylcyclohexane36.Symmetrical? C–CMe3 bond length— axial t-butylcyclohexane37.Closest C–C bond length (Methyl over ring)38Strain energy—equatorial t-butylcyclohexane39.C–CMe3 bond length— equatorial t-butylcyclohexane40.Symmetrical? Draw your assigned substituent on the two structures below and record the calculated strain energy for each structure.Axial:X(CH3)3Equatorial:X(CH3)3Calculated axial strain energy:41.Calculated equatorial strain energy:44.C–X bond length—axial isomer:42. Closest C–C bond distance (methyl over ring):43. Calculated energies for other –X(CH3)3 groups from other students’ calculations:Substituent:Calculations by:Axial strain energy:Equatorial strain energy:C–X bond length—axial isomer: Closest C–C bond distance (methyl over ring):

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Answered: A. Propane Measurements: C1–C2–C3 bond…

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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A. Propane Measurements:

C1–C2–C3 bond angle	1.
H–C2–H bond angle	2.
H–C1–C2 bond angle	3.
H–C1–H bond angle	4.
C–C bond length in propane	5.

B. 2,2-Dimethylbutane Measurements: Carbon numbering here refers to IUPAC numberings.

C2–C3–C4 bond angle	6.
anti-C1–C2–C3 bond angle	7.
gauche-C1–C2–C3 bond angle	8.
C2–C3 bond length	9.

C. Butane Measurements:

Strain energy—anti conformation	10.
C1–C2–C3 bond angle—anti	11.
H–C1–C2 bond angle—anti	12.

DAtA & AnALYSiS Molecular Modeling I 75

C1–C2–C3–H dihedral angle—anti	13.
Strain energy—gauche conformation	14.
C1–C2–C3 bond angle—gauche	15.
C1–C2–C3–C4 dihedral angle—gauche	16.
C1–C4 H–H distance—gauche	17.
H–C1–C2–C3 dihedral angle—gauche	18.

PART II. BOND ROTATION IN BUTANE (STRUCTURES AND ENERGIES)

Dihedral angle—eclipsed conformation	19.
Relative energy—eclipsed	20.
C1–C2–C3 bond angle—eclipsed	21.
C1–C4 H–H distance—eclipsed	22.
C2–C3 bond distance—eclipsed	23.
C1–C2 bond distance—eclipsed	24.
Dihedral angle—second eclipsed conformation	25.
Relative energy—second eclipsed	26.
C1–C2–C3 bond angle—second eclipsed	27.
C2–C3 bond distance—second eclipsed	28.

WRITE-UP

PART III. CONFORMATIONAL ANALYSIS OF SUBSTITUTED CYCLOHEXANES

Strain energy—diaxial 1,2-dimethylcyclohexane	29.
Me–C–C–Me dihedral angle—diaxial	30.
Strain energy—diequatorial 1,2-dimethylcyclohexane	31.
Me–C–C–Me dihedral angle—diequatorial	32.
Strain energy—axial-equatorial 1,2-dimethylcyclohexane	33.
Me–C–C–Me dihedral angle— axial-equatorial	34.

PART IV. COMPARISON OF AXIAL AND EQUATORIAL STRAIN ENERGIES FOR TRIMETHYL-X SUBSTITUENTS A. t-Butylcyclohexane:

Strain energy— axial t-butylcyclohexane	35.
H–C–C–CMe3 dihedral angle— axial t-butylcyclohexane	36.
Symmetrical?
C–CMe3 bond length— axial t-butylcyclohexane	37.
Closest C–C bond length (Methyl over ring)	38
Strain energy— equatorial t-butylcyclohexane	39.
C–CMe3 bond length— equatorial t-butylcyclohexane	40.
Symmetrical?

Draw your assigned substituent on the two structures below and record the calculated strain energy for each structure.

Axial: X(CH3)3	Equatorial: X(CH3)3
Calculated axial strain energy: 41.	Calculated equatorial strain energy: 44.
C–X bond length—axial isomer: 42.
Closest C–C bond distance (methyl over ring): 43.

Calculated energies for other –X(CH3)3 groups from other students’ calculations:

Substituent:	Calculations by:
Axial strain energy:	Equatorial strain energy:
C–X bond length—axial isomer:
Closest C–C bond distance (methyl over ring):

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A. Propane Measurements: C1–C2–C3 bond angle 1. H–C2–H bond angle 2. H–C1–C2 bond angle 3. H–C1–H bond angle 4. C–C bond length in propane 5.