Question

Which nucleophiles would serve to effect the following conversions of 1 -iodopropane? (a) I \(^{-}\) (b) CCCN=[N+]=[N-] (c) CCCS (d) CCCC#N (e) CCCOCCC (f) CCCOc1ccccc1

Short answer

(a) no reaction, (b) CCCN3, (c) CCCSCH2CH3, (d) CCCCH2C≡N, (e) CCCOCH2CH3, (f) CCCOC6H5.

Step-by-step solution

Understand Nucleophiles

A nucleophile is a chemical species that donates an electron pair to form a chemical bond in relation to a reaction. Identify which nucleophile corresponds to the changes described.

Analyze the Given Conversion of 1-iodopropane

For each given nucleophile, check how it will change the 1-iodopropane molecule.

Determine the Product for Each Nucleophile

(a) For I^{-}, no reaction occurs because it would simply replace the iodine with another iodine.(b) For CCCN=[N+]=[N-], it results in the introduction of an azide group. The product will be CCCN3.(c) For CCCS, it introduces an ethyl thio group. The product will be CCCSCH2CH3.(d) For CCCC#N, it results in introduction of a butanenitrile. The product will be CCCCH2C≡N.(e) For CCCOCCC, it introduces an ethoxy group. The product will be CCCOCH2CH3.(f) For CCCOc1ccccc1, it introduces a phenoxy group. The product will be CCCOC6H5.

Key concepts

organic reactions

Organic reactions involve transformations where reactants are converted into products. These reactions occur constantly and are a fundamental part of organic chemistry. To understand organic reactions, one must consider the following:

• The reactants: starting materials involved in the reaction.
• The reagents: substances added to cause the reaction.
• The products: the final substances formed after the reaction.

In the context of our exercise, 1-iodopropane (a reactant) undergoes various reactions with different nucleophiles to form distinct products.

nucleophile

A nucleophile is an atom or molecule that seeks positively charged centers, typically because it has a pair of electrons ready to donate. Nucleophiles are essential in many organic reactions:

• They usually contain lone pairs or π bonds.
• They are attracted to electrophilic (electron-deficient) centers.
• Common nucleophiles include negatively charged ions and molecules with lone pairs.

For example, in our exercise, the nucleophiles provided are:
(a) I^-
(b)CCCN₃
(c) CCCS
(d) CCC≡N
(e) CCCOCH₂CH₃
(f) CCCOC₆H₅.
Each nucleophile interacts differently with the 1-iodopropane molecule to form unique products.

1-iodopropane

1-iodopropane is an organic compound where an iodine atom is attached to the first carbon of a three-carbon chain. It acts as the primary substrate in our reactions:

• The iodine atom is a good leaving group, which means it can easily be replaced by other atoms or groups in reactions.
• When 1-iodopropane reacts with a nucleophile, the iodine atom is replaced, leading to the formation of new compounds.

For each nucleophile, the product formed will differ based on the chemical nature of the nucleophile. Let's analyze some examples from the exercise:

• When reacting with CCCN₃, the product will be 1-azidopropane (CCCN₃).
• When reacting with CCCS, the product will be 1-ethylthiopropane (CCCSCH₂CH₃).
• When reacting with CCC≡N, the product will be 1-cyanopropane (CCCCH₂C≡N).

Understanding these patterns helps predict the outcome of nucleophilic substitution reactions in organic chemistry.