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What are the substitution products of the reaction of 1 -bromobutane with (a) \(\because \mathrm{I}:^{-} ;\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \ddot{\mathrm{O}}:^{-}\); (c) \(\mathrm{N}_{3}^{-}\) (d) : As(CH \(\left._{3}\right)_{3}\); (e) \(\left(\mathrm{CH}_{3}\right)_{2} \ddot{\mathrm{Se}}\) ?

Short Answer

Expert verified
a) 1-iodobutaneb) 1-ethoxybutanec) 1-azidobutaned) Butyl(trimethyl)arsinee) Butyldimethylselenide

Step by step solution

01

- Identify 1-bromobutane

1-bromobutane is a primary alkyl halide with the molecular formula CH鈧僀H鈧侰H鈧侰H鈧侭r.
02

- Understand Substitution Reactions

In substitution reactions, the bromide ion (Br鈦) in 1-bromobutane is replaced by a nucleophile.
03

Step 3a - Reaction with I鈦

Nucleophile: Iodide ion (I鈦)Reaction: CH鈧僀H鈧侰H鈧侰H鈧侭r + I鈦 鈫 CH鈧僀H鈧侰H鈧侰H鈧侷 + Br鈦籔roduct: 1-iodobutane (CH鈧僀H鈧侰H鈧侰H鈧侷)
04

Step 3b - Reaction with CH鈧僀H鈧侽鈦

Nucleophile: Ethoxide ion (CH鈧僀H鈧侽鈦)Reaction: CH鈧僀H鈧侰H鈧侰H鈧侭r + CH鈧僀H鈧侽鈦 鈫 CH鈧僀H鈧侰H鈧侰H鈧侽CH鈧侰H鈧 + Br鈦籔roduct: 1-ethoxybutane (CH鈧僀H鈧侰H鈧侰H鈧侽CH鈧侰H鈧)
05

Step 3c - Reaction with N鈧冣伝

Nucleophile: Azide ion (N鈧冣伝)Reaction: CH鈧僀H鈧侰H鈧侰H鈧侭r + N鈧冣伝 鈫 CH鈧僀H鈧侰H鈧侰H鈧侼鈧 + Br鈦籔roduct: 1-azidobutane (CH鈧僀H鈧侰H鈧侰H鈧侼鈧)
06

Step 3d - Reaction with :As(CH鈧)鈧

Nucleophile: Trimethylarsine (:As(CH鈧)鈧)Reaction: CH鈧僀H鈧侰H鈧侰H鈧侭r + :As(CH鈧)鈧 鈫 CH鈧僀H鈧侰H鈧侰H鈧侫s(CH鈧)鈧 + Br鈦籔roduct: Butyl(trimethyl)arsine (CH鈧僀H鈧侰H鈧侰H鈧侫s(CH鈧)鈧)
07

Step 3e - Reaction with (CH鈧)鈧係e

Nucleophile: Dimethylselenide ((CH鈧)鈧係e)Reaction: CH鈧僀H鈧侰H鈧侰H鈧侭r + (CH鈧)鈧係e 鈫 CH鈧僀H鈧侰H鈧侰H鈧係e(CH鈧)鈧 + Br鈦籔roduct: Butyldimethylselenide (CH鈧僀H鈧侰H鈧侰H鈧係e(CH鈧)鈧)

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

1-bromobutane
1-bromobutane is an organic compound classified as a primary alkyl halide. Its molecular formula is CH鈧僀H鈧侰H鈧侰H鈧侭r. The structure consists of a four-carbon backbone, with a bromine atom (Br) attached to the terminal carbon.
The bromine atom is bonded to the first carbon atom, making it a primary halide. This type of compound is very reactive, especially in substitution reactions.
primary alkyl halide
A primary alkyl halide has the general formula R-CH鈧俋, where R represents an alkyl group and X is a halogen like bromine, chlorine, or iodine. Primary alkyl halides are highly reactive in nucleophilic substitution reactions.
These reactions occur when a nucleophile鈥攁 molecule or ion with a lone pair of electrons鈥攁ttacks the carbon bonded to the halogen, replacing the halide ion with itself. This reactivity is due to the relatively lower steric hindrance around the carbon atom bonded to the halogen, making it easier for nucleophiles to approach and react.
In the case of 1-bromobutane, the molecule reacts with various nucleophiles to form different substitution products, illustrating the versatility and reactivity of primary alkyl halides in chemical reactions.
nucleophile
Nucleophiles are ions or molecules that donate an electron pair to form a chemical bond in reactions. They are characterized by the presence of lone pairs of electrons and a negative charge or a region of high electron density.
Common nucleophiles include ions like iodide (I鈦), ethoxide (CH鈧僀H鈧侽鈦), and azide (N鈧冣伝). These nucleophiles react with electrophilic carbon atoms in alkyl halides, such as the one in 1-bromobutane, to replace the halogen atom.
For instance, when 1-bromobutane reacts with an iodide ion (I鈦), it forms 1-iodobutane (CH鈧僀H鈧侰H鈧侰H鈧侷). Similarly, reactions with other nucleophiles like ethoxide and azide result in the formation of 1-ethoxybutane (CH鈧僀H鈧侰H鈧侰H鈧侽CH鈧侰H鈧) and 1-azidobutane (CH鈧僀H鈧侰H鈧侰H鈧侼鈧), respectively. The reaction mechanism is typically the S\(_\text{N}\)2 type, where the nucleophile attacks the carbon atom and displaces the bromide ion in a single, concerted step.

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