What product is formed when 1-bromopropane reacts with each of the following nucleophiles? d. HS−

Verified step by step guidance

1. Identify the type of reaction: This is a nucleophilic substitution reaction where the nucleophile (HS−) will replace the leaving group (Br−) in 1-bromopropane.
2. Determine the mechanism: Since 1-bromopropane is a primary alkyl halide, the reaction is likely to proceed via an S_N2 mechanism, which involves a single concerted step.
3. Consider the nucleophile: HS− is a strong nucleophile and a weak base, which favors S_N2 reactions.
4. Predict the product: In an S_N2 reaction, the nucleophile attacks the electrophilic carbon from the opposite side of the leaving group, leading to inversion of configuration if the carbon is chiral. Here, HS− will replace Br−, forming propanethiol (CH₃CH₂CH₂SH).
5. Verify the reaction conditions: Ensure that the reaction conditions (such as solvent and temperature) are suitable for an S_N2 reaction to occur efficiently.

Key Concepts

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile attacks an electrophile, resulting in the replacement of a leaving group. In the case of 1-bromopropane, the bromine atom acts as the leaving group, and the nucleophile (HS−) replaces it, forming a new product. Understanding this mechanism is crucial for predicting the outcome of the reaction.

Nucleophiles

Nucleophiles are species that donate an electron pair to form a chemical bond in a reaction. They are typically negatively charged or neutral molecules with lone pairs of electrons. In this question, HS− (hydrosulfide ion) is a strong nucleophile that can effectively attack the carbon atom bonded to the bromine in 1-bromopropane, leading to the formation of a thiol product.

Product Formation

The product formed in a nucleophilic substitution reaction depends on the structure of the starting material and the nature of the nucleophile. In this case, when HS− reacts with 1-bromopropane, the product is propanethiol (C3H7SH), a thiol compound. Recognizing the functional groups and the resulting structure is essential for understanding the implications of the reaction.