Nucleophiles attack at that part of the substrate molecule which is electron deficient. The reaction in which a nucleophile replaces an already existing nucleophile in a molecule is called a nucleophilic substitution reaction. Haloalkanes are substrates in these reactions. In this type of reaction, a nucleophile reacts with a haloalkane (the substrate) having a partial positive charge on the carbon atom bonded to halogen. A substitution reaction takes place, and the halogen atom, called the leaving group, departs as a halide ion. Since the substitution reaction is initiated by a nucleophile, it is called a nucleophilic substitution reaction.
\(Nu^− +C-X →C-Nu+X^−\)
When sodium hydroxide (NaOH) reacts with a haloalkane (R-X), the hydroxide ion (OH-) acts as a nucleophile and replaces the halogen (X) atom in a nucleophilic substitution reaction. This leads to the formation of an alcohol (R-OH) and a halide ion (X-). The reaction can be represented as follows:
R-X + NaOH → R-OH + NaX
In this reaction, the halogen (X) is displaced by the hydroxide ion (OH-) through a substitution process, forming an alcohol (R-OH) and a sodium halide (NaX) as the products. The type of substitution that occurs depends on the structure of the haloalkane and the conditions of the reaction. In general, primary haloalkanes undergo SN2 (bimolecular nucleophilic substitution), while secondary and tertiary haloalkanes are more likely to undergo SN1 (unimolecular nucleophilic substitution).
Thus, the major product of this reaction is an alcohol (R-OH). This type of reaction is important in organic synthesis, particularly in the preparation of alcohols from haloalkanes.
When potassium cyanide (KCN) reacts with a haloalkane (R-X), the cyanide ion (CN-) acts as a nucleophile in a nucleophilic substitution reaction. The cyanide ion (CN-) replaces the halogen atom (X) in the haloalkane, resulting in the formation of a nitrile (R-CN) and a halide ion (X-). The reaction can be represented as follows:
R-X + KCN → R-CN + KX
This nucleophilic substitution involves the displacement of the halogen atom (X) by the cyanide ion (CN-), forming a nitrile group (C≡N) in the product. The type of substitution mechanism that occurs generally depends on the structure of the haloalkane and reaction conditions. Primary haloalkanes typically undergo SN2 (bimolecular nucleophilic substitution), while secondary or tertiary haloalkanes may proceed via the SN1 mechanism, depending on factors such as the stability of the carbocation intermediate.
Thus, the major product of this reaction is a nitrile (R-CN). Nitriles are important intermediates in organic synthesis and can be further converted into other functional groups, such as carboxylic acids or amides.
When silver cyanide (AgCN) reacts with a haloalkane (R-X), the cyanide ion (CN-) acts as a nucleophile and replaces the halogen atom (X) in a nucleophilic substitution reaction. This leads to the formation of an isonitrile (R-NC) and silver halide (AgX) as a byproduct. The reaction can be represented as follows:
R-X + AgCN → R-NC + AgX
In this reaction, the cyanide ion (CN-) attacks the carbon atom attached to the halogen atom in the haloalkane. The halogen atom is displaced, and the result is the formation of an isonitrile (R-NC) along with the release of silver halide (AgX). This reaction follows the SN2 mechanism, where the nucleophile (CN-) directly attacks the carbon atom opposite the leaving group (X), resulting in an inversion of configuration at the carbon center.
Thus, the major product of this reaction is an isonitrile (R-NC). Isonitriles are important intermediates in organic synthesis and can be used in further reactions to create a variety of nitrogen-containing compounds.
When potassium nitrite (KNO2) reacts with a haloalkane (R-X), the nitrite ion (\(NO_2^-\)) acts as a nucleophile and replaces the halogen atom (X) in a nucleophilic substitution reaction. This leads to the formation of an alkyl nitrite (R-ONO) and a halide ion (X-). The reaction can be represented as follows:
R-X + KNO2 → R-ONO + KX
In this reaction, the nitrite ion (NO2-) acts as a nucleophile and displaces the halogen atom (X) from the haloalkane through a nucleophilic substitution mechanism, forming an alkyl nitrite (R-ONO) and a halide ion (X-) as a byproduct. This type of substitution typically follows the SN2 mechanism, where the nucleophile attacks the carbon atom from the opposite side of the leaving group.
Thus, the major product of this reaction is an alkyl nitrite (R-ONO). Alkyl nitrites are important compounds used in various chemical processes and can be further reacted to form other useful organic molecules.
When ammonia (NH3) reacts with a haloalkane (R-X), the nitrogen atom in ammonia acts as a nucleophile and replaces the halogen atom (X) in a nucleophilic substitution reaction. This results in the formation of a primary amine (R-NH2) and a hydrogen halide (HX). The reaction can be represented as follows:
R-X + NH3 → R-NH2 + HX
In this reaction, the nucleophilic attack is carried out by the ammonia molecule, where the lone pair of electrons on the nitrogen atom in ammonia displaces the halogen atom (X). This leads to the formation of a primary amine (R-NH2) and a hydrogen halide (HX) as a byproduct.
Thus, the major product of this reaction is a primary amine (R-NH2). Primary amines are important functional groups in organic synthesis and can be further modified in various reactions to produce other nitrogen-containing compounds.
Total number of nucleophiles from the following is: \(\text{NH}_3, PhSH, (H_3C_2S)_2, H_2C = CH_2, OH−, H_3O+, (CH_3)_2CO, NCH_3\)
In the following substitution reaction:
(A) Draw the structure of the major monohalo product for each of the following reactions: \vspace{5pt} (a) \includegraphics[]{26a.png}
Propene to 1-Iodopropane
List-I | List-II | ||
A | Megaliths | (I) | Decipherment of Brahmi and Kharoshti |
B | James Princep | (II) | Emerged in first millennium BCE |
C | Piyadassi | (III) | Means pleasant to behold |
D | Epigraphy | (IV) | Study of inscriptions |