Question

Show reagents to convert bromocyclopentane to each of the following compounds.

Short answer

Answer: The reagents needed are as follows: 1. Cyclopentene: potassium tert-butoxide (t-BuOK) 2. Cyclopentanol: water (H2O) in the presence of an acid catalyst as conditions (for example, H2SO4 or HCl) 3. Cyclopentanone: sodium cyanide (NaCN) followed by hydrolysis using an acid catalyst and water (H2O, H2SO4, heat).

Step-by-step solution

1. Conversion of Bromocyclopentane to Cyclopentene:

To convert bromocyclopentane to cyclopentene, we will need a reagent that promotes a dehalogenation reaction, which removes the bromine from the molecule and forms a double bond. The required reagent for this transformation is a strong base, such as potassium tert-butoxide (t-BuOK).

2. Conversion of Bromocyclopentane to Cyclopentanol:

To convert bromocyclopentane to cyclopentanol, we will need a reagent that replaces the bromine atom with a hydroxyl group (-OH). This substitution reaction requires the use of a suitable nucleophile, which for this case can be water (H2O) in the presence of an acid catalyst as conditions (for example, H2SO4 or HCl) to form cyclopentanol via Sn1 reaction mechanism.

3. Conversion of Bromocyclopentane to Cyclopentanone:

To convert bromocyclopentane to cyclopentanone, we first need to substitute the bromine atom with a nitrile group (-CN). This is done using a nucleophile like sodium cyanide (NaCN) in an SN2 reaction. After that, we need to hydrolyze the nitrile group into a carbonyl group (C=O). The hydrolysis of the nitrile group can be done using an acid catalyst and water (H2O, H2SO4, heat). In summary, the reagents needed to convert bromocyclopentane to the example compounds given are: 1. Cyclopentene: potassium tert-butoxide (t-BuOK) 2. Cyclopentanol: water (H2O) in the presence of an acid catalyst as conditions (for example, H2SO4 or HCl) 3. Cyclopentanone: sodium cyanide (NaCN) followed by hydrolysis using an acid catalyst and water (H2O, H2SO4, heat).