Alkanes conformations Sawhorse and Newman projections and halogenation - One Line Questions

1. In the Newman projection of ethane, what is the dihedral angle between hydrogens on adjacent carbons in the eclipsed conformation? — 0 degrees
2. What is the dihedral angle between hydrogens on adjacent carbons in the staggered conformation of ethane? — 60 degrees
3. What is the main product of the free radical bromination of isobutane? — 2-Bromo-2-methylpropane
4. What is the main product when n-pentane is subjected to free radical chlorination? — A mixture of isomers
5. What is the primary product when propane is chlorinated under UV light? — 1-Chloropropane
6. During the free radical chlorination of methane, what is the relative rate of substitution of hydrogen atoms in the order primary:secondary:tertiary? — 1:3:5
7. The relative rate of attack on primary, secondary, and tertiary C-H bonds by chlorine radical is approximately: — 1:3.8:5.2
8. The relative rate of attack on primary, secondary, and tertiary C-H bonds by bromine radical is approximately: — 1:80:1600
9. The energy difference between the chair and boat conformations of cyclohexane is approximately: — 20-30 kcal/mol
10. What is the term for the energy difference between different conformations of a molecule? — Conformational energy
11. The stability order of alkyl carbocations is the same as the stability order of: — Alkyl radicals
12. Which of the following is a synclinal conformation of butane? — Gauche
13. Which statement best describes the relative stability of butane conformations? — Anti > Gauche > Eclipsed
14. The most stable conformation of cyclohexane is the: — Chair conformation
15. Why is the selectivity of bromine radicals much higher than chlorine radicals in alkane halogenation? — Bromine radical is less reactive and more selective
16. Which conformation of cyclohexane has higher energy due to the steric repulsion between flagpole hydrogens? — Boat
17. Which step is the first step in the free radical halogenation of methane with chlorine? — Cl2 + UV light → 2Cl•
18. Which of the following is a termination step in the free radical chlorination of methane? — 2Cl• → Cl2
19. Which step is the propagation step in the free radical halogenation of methane? — •CH3 + Cl2 → CH3Cl + Cl•
20. Which step terminates the free radical chain reaction in alkane halogenation? — Combination of any two radicals
21. Which conformation of ethane is the most stable? — Staggered
22. The 'anti' conformation of butane is a type of which broader conformational class? — Staggered
23. The 'gauche' conformation of butane is a type of which broader conformational class? — Staggered
24. Which of the following reactions is characteristic of alkanes? — Free radical substitution
25. Which group experiences greater 1,3-diaxial strain in cyclohexane? — Axial methyl group
26. Which halogen is most reactive in the free radical substitution of alkanes? — Fluorine
27. Which halogen is least reactive and requires more forcing conditions for free radical substitution of alkanes? — Iodine
28. In a Sawhorse projection, the bonds are viewed from which angle? — Side-on
29. What is the primary driving force for the formation of free radicals in halogenation? — Homolytic cleavage of a covalent bond
30. What is the primary reason for the difference in stability between eclipsed and staggered conformations? — Steric hindrance and torsional strain
31. The free radical halogenation of alkanes is a method for: — Functionalizing alkanes
32. The halogenation of alkanes with iodine is generally not synthetically useful because: — The reaction is reversible and the reverse reaction is favored
33. In the free radical halogenation of a symmetrical alkane, how many distinct monohalogenated products are possible? — One
34. In the chair conformation of cyclohexane, axial bonds are oriented: — Perpendicular to the ring plane
35. In the chair conformation of cyclohexane, equatorial bonds are oriented: — Parallel to the ring plane
36. The stability order of alkyl radicals is: — Tertiary > Secondary > Primary
37. The interconversion of chair conformations of cyclohexane is called: — Ring flip
38. Which projection method explicitly shows the dihedral angles between substituents on adjacent carbons? — Newman projection
39. Why is the secondary hydrogen in propane more likely to be substituted than the primary hydrogen during free radical chlorination? — Secondary radical is more stable
40. The halogenation of alkanes typically proceeds via which mechanism? — Free radical chain mechanism
41. Which conformation of ethane has the highest potential energy? — Eclipsed
42. The eclipsed conformation where the largest groups are directly aligned is called: — Syn-periplanar
43. What is the term for the conformation where substituents on adjacent carbons are aligned in the same plane? — Eclipsed
44. In the eclipsed conformation of ethane, the electron-electron repulsion between the bonding electrons of adjacent C-H bonds is known as: — Torsional strain
45. What is required to initiate the free radical halogenation of alkanes? — Heat or UV light
46. In the Newman projection of butane, which conformation has the two methyl groups positioned 180 degrees apart? — Anticlinic
47. The staggered conformation where the largest groups are 180 degrees apart is called: — Anti-periplanar
48. The staggered conformation where the largest groups are 60 degrees apart is called: — Synclinal (Gauche)
49. Which of the following is NOT a type of strain in molecular conformations? — Aromatic strain
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