Which nucleophile, when reacted with 1-bromopropane (CH3CH2CH2Br), would produce a thiol?
OH-
SH-
I-
-OCH3
To determine which nucleophile would produce a thiol when reacted with 1-bromopropane (CH3CH2CH2Br), we need to understand the properties and reactions of nucleophiles.
A nucleophile is a chemical species with a lone pair of electrons that can donate them to an electrophile, creating a new covalent bond. The reactivity of a nucleophile is influenced by factors such as its electronegativity, size, and charge.
In this case, we want to form a thiol, which is an organic compound that contains a sulfur atom bonded to a hydrogen atom (R-SH). So, we need a nucleophile that can donate a pair of electrons to the carbon atom in 1-bromopropane, resulting in the replacement of the bromine atom by a sulfur atom.
Let's analyze the potential nucleophiles given:
1. OH-: This is the hydroxide ion, which is a strong nucleophile. However, it would not produce a thiol when reacted with 1-bromopropane. Instead, it would result in the formation of an alcohol (CH3CH2CH2OH) due to the substitution of the bromine atom by the hydroxide group (OH).
2. SH-: This is the sulfide ion, which is a strong nucleophile and exactly what we are looking for. When reacted with 1-bromopropane, it will substitute the bromine atom with sulfur, resulting in the formation of 1-propanethiol (CH3CH2CH2SH). Therefore, SH- is the correct choice for producing a thiol.
3. I-: This is the iodide ion, which is also a strong nucleophile. However, it would not produce a thiol when reacted with 1-bromopropane. It would result in the formation of 1-iodopropane (CH3CH2CH2I) due to the substitution of the bromine atom by the iodide group (I).
4. -OCH3: This is the methoxide ion, which is a strong nucleophile. However, it would not produce a thiol when reacted with 1-bromopropane. It would result in the formation of 1-methoxypropane (CH3CH2CH2OCH3) due to the substitution of the bromine atom by the methoxide group (OCH3).
In conclusion, the nucleophile that, when reacted with 1-bromopropane, would produce a thiol is SH-.
To produce a thiol (R-SH) from 1-bromopropane (CH3CH2CH2Br), we need a nucleophile that can substitute the bromine atom with a thiol group (-SH). The correct nucleophile in this case is SH- (sulfide ion).
The reaction would proceed as follows:
CH3CH2CH2Br + SH- → CH3CH2CH2SH + Br-
Here, the nucleophile SH- attacks the carbon atom bonded to the bromine atom, resulting in the substitution of bromine with a thiol group (-SH).