Alkanes conformations Sawhorse and Newman projections and halogenation - Question Bank

1. Which statement best describes the relative stability of butane conformations?
A) Anti > Gauche > Eclipsed
B) Gauche > Anti > Eclipsed
C) Eclipsed > Anti > Gauche
D) Anti > Eclipsed > Gauche
2. The free radical halogenation of alkanes is a method for:
A) Introducing unsaturation
B) Functionalizing alkanes
C) Breaking C-C bonds
D) Cyclization
3. Which of the following is NOT a type of strain in molecular conformations?
A) Torsional strain
B) Steric strain
C) Angle strain
D) Aromatic strain
4. What is the term for the conformation where substituents on adjacent carbons are aligned in the same plane?
A) Staggered
B) Eclipsed
C) Skew
D) Anti
5. The energy difference between the chair and boat conformations of cyclohexane is approximately:
A) 5-10 kcal/mol
B) 10-15 kcal/mol
C) 20-30 kcal/mol
D) 50-60 kcal/mol
6. Which conformation of cyclohexane has higher energy due to the steric repulsion between flagpole hydrogens?
A) Chair
B) Boat
C) Twist-boat
D) Half-chair
7. What is the main product when n-pentane is subjected to free radical chlorination?
A) 1-Chloropentane
B) 2-Chloropentane
C) 3-Chloropentane
D) A mixture of isomers
8. In the free radical halogenation of a symmetrical alkane, how many distinct monohalogenated products are possible?
A) One
B) Two
C) Three
D) Depends on the halogen
9. The stability order of alkyl carbocations is the same as the stability order of:
A) Alkyl radicals
B) Alkyl carbanions
C) Alkenes
D) Alkynes
10. The stability order of alkyl radicals is:
A) Primary > Secondary > Tertiary
B) Tertiary > Secondary > Primary
C) Secondary > Primary > Tertiary
D) Primary > Tertiary > Secondary
11. Which of the following is a termination step in the free radical chlorination of methane?
A) Cl2 + hv → 2Cl•
B) Cl• + CH4 → HCl + •CH3
C) •CH3 + Cl2 → CH3Cl + Cl•
D) 2Cl• → Cl2
12. What is the primary driving force for the formation of free radicals in halogenation?
A) Homolytic cleavage of a covalent bond
B) Heterolytic cleavage of a covalent bond
C) Nucleophilic attack
D) Electrophilic attack
13. Which group experiences greater 1,3-diaxial strain in cyclohexane?
A) Equatorial methyl group
B) Axial methyl group
C) Axial hydrogen
D) Equatorial hydrogen
14. The interconversion of chair conformations of cyclohexane is called:
A) Rotation
B) Inversion
C) Ring flip
D) Tautomerization
15. In the chair conformation of cyclohexane, equatorial bonds are oriented:
A) Perpendicular to the ring plane
B) Parallel to the ring plane
C) Along the ring axis
D) Vertically upwards
16. In the chair conformation of cyclohexane, axial bonds are oriented:
A) Parallel to the ring plane
B) Perpendicular to the ring plane
C) At an angle to the ring plane
D) Along the ring edge
17. The most stable conformation of cyclohexane is the:
A) Boat conformation
B) Twist-boat conformation
C) Chair conformation
D) Half-chair conformation
18. Which of the following is a synclinal conformation of butane?
A) Anti
B) Gauche
C) Syn-periplanar
D) Fully eclipsed
19. In the eclipsed conformation of ethane, the electron-electron repulsion between the bonding electrons of adjacent C-H bonds is known as:
A) Steric strain
B) Torsional strain
C) Angle strain
D) Van der Waals strain
20. What is the term for the energy difference between different conformations of a molecule?
A) Activation energy
B) Reaction energy
C) Conformational energy
D) Bond energy
21. The halogenation of alkanes with iodine is generally not synthetically useful because:
A) Iodine radical is too reactive
B) The reaction is reversible and the reverse reaction is favored
C) Iodine is too expensive
D) No free radical is formed
22. What is the main product of the free radical bromination of isobutane?
A) 1-Bromobutane
B) 2-Bromobutane
C) 2-Bromo-2-methylpropane
D) 1-Bromo-2-methylpropane
23. Why is the selectivity of bromine radicals much higher than chlorine radicals in alkane halogenation?
A) Bromine radical is smaller
B) Bromine radical is less reactive and more selective
C) Bromine radical is more reactive and less selective
D) Activation energy for bromine radical attack is lower
24. The relative rate of attack on primary, secondary, and tertiary C-H bonds by bromine radical is approximately:
A) 1:1:1
B) 1:80:1600
C) 1:4:5
D) 5:3:1
25. The relative rate of attack on primary, secondary, and tertiary C-H bonds by chlorine radical is approximately:
A) 1:1:1
B) 1:4:5
C) 1:3.8:5.2
D) 5:3:1
26. Why is the secondary hydrogen in propane more likely to be substituted than the primary hydrogen during free radical chlorination?
A) Secondary radical is more stable
B) Primary radical is more stable
C) Secondary radical is more reactive
D) Primary radical is more reactive
27. What is the primary product when propane is chlorinated under UV light?
A) 1-Chloropropane
B) 2-Chloropropane
C) 1,1-Dichloropropane
D) 1,2-Dichloropropane
28. Which halogen is least reactive and requires more forcing conditions for free radical substitution of alkanes?
A) Fluorine
B) Chlorine
C) Bromine
D) Iodine
29. Which halogen is most reactive in the free radical substitution of alkanes?
A) Fluorine
B) Chlorine
C) Bromine
D) Iodine
30. During the free radical chlorination of methane, what is the relative rate of substitution of hydrogen atoms in the order primary:secondary:tertiary?
A) 1:1:1
B) 1:3:5
C) 5:3:1
D) 1:5:3
31. Which step terminates the free radical chain reaction in alkane halogenation?
A) Cl2 + UV light → 2Cl•
B) Cl• + CH4 → HCl + •CH3
C) •CH3 + Cl2 → CH3Cl + Cl•
D) Combination of any two radicals
32. Which step is the propagation step in the free radical halogenation of methane?
A) Cl2 + UV light → 2Cl•
B) Cl• + CH4 → HCl + •CH3
C) •CH3 + Cl2 → CH3Cl + Cl•
D) Cl• + Cl• → Cl2
33. Which step is the first step in the free radical halogenation of methane with chlorine?
A) Cl• + CH4 → HCl + •CH3
B) Cl2 + UV light → 2Cl•
C) •CH3 + Cl2 → CH3Cl + Cl•
D) •CH3 + Cl• → CH3Cl
34. What is required to initiate the free radical halogenation of alkanes?
A) Strong acid catalyst
B) Heat or UV light
C) High pressure
D) Oxidizing agent
35. The halogenation of alkanes typically proceeds via which mechanism?
A) SN1
B) SN2
C) Free radical chain mechanism
D) Addition-elimination
36. Which of the following reactions is characteristic of alkanes?
A) Electrophilic addition
B) Nucleophilic substitution
C) Free radical substitution
D) Electrophilic substitution
37. The staggered conformation where the largest groups are 60 degrees apart is called:
A) Syn-periplanar
B) Anti-periplanar
C) Synclinal (Gauche)
D) Anticlinic
38. The staggered conformation where the largest groups are 180 degrees apart is called:
A) Syn-periplanar
B) Anti-periplanar
C) Synclinal
D) Anticlinic
39. The eclipsed conformation where the largest groups are directly aligned is called:
A) Staggered
B) Syn-periplanar
C) Anti-periplanar
D) Synclinal
40. Which projection method explicitly shows the dihedral angles between substituents on adjacent carbons?
A) Sawhorse projection
B) Newman projection
C) Fischer projection
D) Kekulé structure
41. In a Sawhorse projection, the bonds are viewed from which angle?
A) Head-on
B) Side-on
C) Top-down
D) Bottom-up
42. What is the primary reason for the difference in stability between eclipsed and staggered conformations?
A) Hydrogen bonding
B) Resonance stabilization
C) Steric hindrance and torsional strain
D) Aromaticity
43. The 'gauche' conformation of butane is a type of which broader conformational class?
A) Eclipsed
B) Staggered
C) Fully eclipsed
D) Syn-periplanar
44. In the Newman projection of butane, which conformation has the two methyl groups positioned 180 degrees apart?
A) Syn-periplanar
B) Anticlinic
C) Synclinal
D) Anticlinal
45. The 'anti' conformation of butane is a type of which broader conformational class?
A) Eclipsed
B) Staggered
C) Skew
D) Fully eclipsed
46. Which conformation of ethane has the highest potential energy?
A) Staggered
B) Eclipsed
C) Anti
D) Gauche
47. What is the dihedral angle between hydrogens on adjacent carbons in the staggered conformation of ethane?
A) 0 degrees
B) 60 degrees
C) 120 degrees
D) 180 degrees
48. In the Newman projection of ethane, what is the dihedral angle between hydrogens on adjacent carbons in the eclipsed conformation?
A) 0 degrees
B) 60 degrees
C) 120 degrees
D) 180 degrees
49. Which conformation of ethane is the most stable?
A) Eclipsed
B) Staggered
C) Skew
D) Partially eclipsed