Radical Reactions
The three general steps in any radical chain mechanism.
What are initiation, propagation, and termination?
The four main categories of organic reaction types.
What are addition, elimination, substitution, and rearrangement?
The meaning of a curved arrow in an organic mechanism.
What is the movement of an electron pair?
The reagent commonly used to convert an alcohol into an alkyl chloride in substitution reactions.
What is SOCl₂?
The conjugate base of water.
What is hydroxide ion (OH⁻)?
The type of hydrogen most reactive in radical halogenation due to the stability of its radical.
What is tertiary hydrogen?
The classification of a reaction that converts an alcohol to an alkyl chloride using SOCl₂ and pyridine.
What is substitution?
The side of a substrate that the nucleophile attacks in an SN2 reaction.
What is the backside?
The solvent most favorable for SN2 reactions because it does not stabilize cations.
What is a polar aprotic solvent such as DMF?
The stronger acid between HCl (pKa = –7) and acetic acid (pKa = 5).
What is HCl?
The homolytic bond cleavage that begins the chlorination of methane.
What is Cl₂ → 2 Cl·?
A reaction that forms a π bond by removing atoms or groups from adjacent carbons.
What is elimination?
The reason tertiary substrates are poor candidates for SN2 mechanisms.
What is steric hindrance?
The reagent that converts an alkyl halide into a nitrile, proceeding through an SN2 mechanism.
What is NaCN in DMF?
The compound most acidic among an alkyne (pKa ≈ 25), alkene (44), and alkane (55).
What is an alkyne?
The type of radical halogenation that selectively targets allylic positions, often using NBS and light.
What is allylic bromination?
The reaction type used when two molecular fragments join under basic conditions in MeCN, as in the final step of dofetilide synthesis.
What is substitution?
The step in a bromination mechanism that generates a new radical and continues the chain reaction.
What is propagation?
The type of solvent that best promotes SN1 reactions by stabilizing carbocations.
What is a polar protic solvent such as water or alcohol?
The hybridization that stabilizes the conjugate base of a terminal alkyne.
What is sp hybridization?
The reaction step responsible for forming ethane as a side product during methane chlorination.
What is a termination step involving methyl radical coupling?
The reason (S)-2-butanol must first be converted to (R)-2-bromobutane before reacting with NaN₃ to give (S)-2-azidobutane.
What is because –OH is a poor leaving group and SN2 causes inversion?
The high-energy points on an energy diagram that represent unstable arrangements of atoms during a reaction.
What are transition states?
The factor that determines whether a substrate reacts by SN1 or SN2
What is the degree of substitution (the structure of the substrate)?
The stronger base between NaOH and NaNH₂ when deprotonating a terminal alkyne.
What is NaNH₂?