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Magazine Chapter 7: PROBLEM 7.41 (page 290)
Question: Draw the products formed when each alkyl halide is treated with NaCN.
a.
b.
Short Answer
Step by step solution
Ball-and-stick model
Deduce the chemical structure from the given ball-and-stick model using the number of bonds attached to the particular ball.
Nucleophilic substitution reactions
The base or the nucleophile replaces the halide ion from the alkyl halide
Products of the given reactions
In each of the given compounds, the given black balls are tetravalent and must be symbolizing the carbon atoms. The given white balls are single-bonded and must be hydrogen atoms.
The red ball is single-bonded and much larger than the carbon atoms. The red ball must be symbolizing the bromine atom.
In each of the following reactions, CN-being the stronger nucleophile substitutes the bromine atom via the SN2 mechanism.
a. When compound (a) is treated with NaCN, inversion of symmetry takes place; the CN- ion attacks the alkyl halide from the opposite side of the halide atom. Thus, the skeletal structure of the compound is formed, which is shown below:
b. When compound (a) is treated with NaCN, inversion of symmetry takes place; the CN- ion attacks the alkyl halide from the opposite side of the halide atom. Thus, the skeletal structure of the compound is formed, which is shown below:
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