Which of the following solvents would NOT react violently with LiAlH4?

Lithium aluminum hydride (LiAlH4) is a strong reducing agent that can react violently with certain types of solvents, particularly those that contain protic functional groups. The reason aromatic hydrocarbons would not react violently with LiAlH4 lies in their lack of reactive functional groups that can readily protonate or interact with the reducing agent.

Aromatic hydrocarbons consist mainly of carbon and hydrogen with a stable pi-electron system, making them relatively inert to nucleophiles like LiAlH4. In contrast, ethers, alcohols, and aldehydes contain oxygen atoms with lone pairs that are capable of protonating the hydride ion from LiAlH4, resulting in potentially violent reactions. Ethers can also undergo cleavage under these conditions, while alcohols and aldehydes can lead to the production of rapid gas evolution or increase in pressure due to the formation of alkoxides or other intermediates.

Therefore, aromatic hydrocarbons remain stable solvents for reactions involving LiAlH4, whereas the presence of functional groups in ethers, alcohols, and aldehydes increases the risk of reaction and subsequent hazards. Thus, the reasoning is based on the stability of aromatic hydrocarbons and their inability to engage in violent reactions with LiAlH