Question: Device a synthesis of each compound from an alkyl halide using any other organic or inorganic reagents.

a.

b.

c.

d.

Short Answer

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ANSWER

a.

b.

c.

d.

Step by step solution

01

Alkyl halide

The alkyl halide is an organic compound that is represented by the alkyl group bonded with any halogen atom (F, Cl, Br, I).

The halogen atoms are more electronegative than carbon. Therefore, it generates the electrophilic carbon at the position where the C-X bond.

02

Chemical properties of alkyl halide

The alkyl halide undergoes a nucleophilic substitution reaction in which a nucleophile attacks the carbon of the C-X bond (X is the halogen atom).

  • If the attack of the incoming nucleophile occurs directly on the alkyl halide, it is a bimolecular substitution (SN2) .
  • If the attack of nucleophile occurs on the carbocation intermediate of alkyl halide, it is a unimolecular substitution.
  • In the bimolecular substitution, the stereochemistry of the product gets changed, and in the unimolecular substitution, the stereochemistry remains the same.
03

Mechanism

The nucleophile in the nucleophilic reaction replaces the leaving group present in the substrate.

a.

Substituted product

So, in the given reaction, the alkyl halide is 1-chloro-4-methylpentane, and the leaving group is chloride in this compound. The -SH group attacks at the carbon-bearing chloride bond (C-Cl). Therefore, the product is formed by the elimination of chloride as shown below:

Nucleophilic substitution reaction

b.

Substituted product

So, in the given reaction, the alkyl halide is 1-chloropropane, and the leaving group is chloride in this compound. The -OCH2CH2CH3group attacks at the carbon-bearing chloride bond (C-Cl). Therefore, the product is formed by

the elimination of chloride as shown below:

Nucleophilic substitution reaction

c.

Substituted product

So, in the given reaction, the alkyl halide is 1-chloroethane, and the leaving group is chloride in this compound. The -CN group attacks at the carbon-bearing chloride bond (C-Cl). Therefore, the product is formed by the elimination of chloride as shown below:

Nucleophilic substitution reaction

d.

Substituted product

So, in the given reaction, the alkyl halide is 1-chloroethane, and the leaving group is chloride in this compound. The -OCOCH3 group attacks the carbon-bearing chloride bond (C-Cl). Therefore, the product is formed by the elimination of chloride as shown below:

Nucleophilic substitution reaction

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Most popular questions from this chapter

Question: Consider the following SN2 reaction.

  1. Draw a mechanism using curved arrows.
  2. Draw an energy diagram. Label the axes, the reactants, products, Ea , and H°. Assume that the reaction is exothermic.
  3. Draw the structure of the transition state.
  4. What is the rate equation?
  5. What happens to the reaction rate in each of the following instances? [1] The leaving group is changed from Br-to I-;[2] The solvent is changed from acetone to CH3CH2OH ; [3] The alkyl halide is changed from CH3(CH2)4Br to CH3CH2CH2CH(Br)CH3 ; [4] The concentration of CN- is increased by a factor of five; and [5] The concentrations of both the alkyl halide and CN-are increased by a factor of five.

Question: Draw the eight constitutional isomers having the molecular formula C5H11Cl .

  1. Give the IUPAC name for each compound (ignoring R and S designations).
  2. Classify each alkyl halide as 1°,2°or3°.
  3. Label any stereogenic centers.
  4. For each constitutional isomer that contains a stereogenic center, draw all possible stereoisomers, and label each stereogenic center as R or S.

Question: Give the IUPAC name for each compound.

a.

b.

c,

d.

e.

f.

Question: In some nucleophilic substitutions under SN1 conditions, complete racemization does not occur, and a small excess of one enantiomer is present. For example, treatment of optically pure 1-bromo-1-phenylpropane with water forms 1-phenylpropan-1-ol. a. Calculate how much of each enantiomer is present using the given optical rotation data. b. Which product predominates—the product of inversion or the product of retention of configuration? c. Suggest an explanation for this phenomenon.

Question: Which molecules contain good leaving groups?

a.

b.

c.

d.

CH3-CH3

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