Alcohols generally do substitution reactions with __________________. (select all that apply)

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Question restatement: The prompt asks which types of species alcohols generally undergo substitution reactions with, and it allows selecting more than one option. Options provided: poor nucleophiles, weakly basic nucleophiles, strongly basic nucleophiles, nucleophilic acids, non-nucleophilic acids, none of these.

Option 1: poor nucleophiles.
- Rationale: Alcohols themselves are poor nucleophiles due to the oxygen’s lone pairs being relatively stabilized by hydrogen bonding and resonance-within the molecule; in many substitution mechanisms (SN1/SN2), they react sluggishly unless activated (e.g., by protonation or conversion to a better leaving group). As a general rule, alcohols are not strong nucleophiles, so describing them as poor nucleophiles aligns with common organic chemistry understanding.

Option 2: weakly basic nucleophiles.
- Rationale: Alcohols are also weak bases, since the conjugate bases (alkoxides) are stronger bases than the neutral alcohols but within typical solvent contexts they act as weak nucleophiles. In substitution chemistry, reagents that are weak bases often participate in SN1/SN2 routes when leaving groups or conditions favor carbocation formation or relatively soft electrophiles. Therefore, labeling alcohols as weakly basic nucleophiles is consistent with their dual character: modest basicity and modest nucleophilicity.

Option 3: strongly basic nucleophiles.
- Rationale: Strongly basic nucleophiles (e.g., alkoxides in highly basic media) can indeed behave as nucleophiles, but the descriptor strongly basic suggests a reactivity profile that is higher than that of neutral alcohols under typical substitution conditions. In many standard substitution contexts, neutral alcohols are not as nucleophilic as strongly basic species; thus, this option is generally not the typical description of alcohols undergoing substitution. It overstates their nucleophilicity.

Option 4: nucleophilic acids.
- Rationale: Acids are not nucleophiles; a nucleophile donates electron density to an electrophilic center, whereas acids are proton donors and electophilic in many substitutions, not nucleophilic. The phrase nucleophilic acids is unusual and misleading in standard substitution chemistry; alcohols do not behave as nucleophilic acids.

Option 5: non-nucleophilic acids.
- Rationale: Non-nucleophilic acids are even less likely to participate as nucleophiles in substitution reactions, since the term implies they are not nucleophilic at all. Since alcohols are neutral and can act as nucleophiles under certain conditions, this label would not accurately describe their behavior in substitution contexts.

Option 6: none of these.
- Rationale: Since there are plausible descriptors among the choices that align with the typical behavior of alcohols (namely poor nucleophiles and weakly basic nucleophiles), selecting none would ignore valid characterizations. Therefore this option is not appropriate if the prior options capture real aspects of alcohol reactivity.

Overall assessment: Alcohols are not strong nucleophiles; they are better described as poor nucleophiles and often weakly basic. They are not correctly described as strongly basic nucleophiles, nucleophilic acids, or non-nucleophilic acids in the standard substitution context. This means the two statements that align with common understanding are that alcohols behave as poor nucleophiles and as weakly basic nucleophiles in substitution scenarios. The remaining options describe reactivity profiles that do not fit the typical behavior of alcohols in substitution chemistry.

CHE 008B A01 SS1 2025 Lecture 1/2 - Alcohols and HX

Alcohols generally do substitution reactions with __________________. (select all that apply)

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