Outline the following synthesis:
a) 2 – methyl propene -> 2-methyl-2-propanol.
b) 3 –ethylpentene -> carbon dioxide, water and 2-ethylbutanoic acid.
c) 2 methyl-2-pentene -> 2-chloro-2-methylpetane and 3-chloro-2-methylpentane
d) 1-ethylcyclohexene -> 1-ethyl-1-hydroxy-2-chlorocyclohexane, 1-ethyl-1-choro-2-hydroxycyclohexane and 1-ethyl-1,2-dichlorocyclohexane
a) To synthesize 2-methyl-2-propanol from 2-methyl propene, you would need to perform an addition reaction where water is added across the double bond. This reaction is known as hydration. Here are the steps to follow:
1. Start with 2-methyl propene.
2. Mix it with water (H2O) in the presence of an acid catalyst, such as sulfuric acid (H2SO4).
3. The acid catalyst will protonate the double bond, making it more susceptible to nucleophilic attack by water.
4. Water will attack the more substituted carbon of the double bond, forming a carbocation intermediate.
5. The carbocation intermediate will then react with water, generating the final product, 2-methyl-2-propanol.
b) To synthesize carbon dioxide, water, and 2-ethylbutanoic acid from 3-ethylpentene, you would need to perform oxidation and hydrolysis reactions, as well as oxidation of the resulting hydroxy acid. Here are the steps:
1. Start with 3-ethylpentene.
2. React it with an excess of ozone (O3) to form ozonide intermediate.
3. The ozonide intermediate can be reduced with dimethyl sulfide (CH3)2S, yielding a mixture of carbonyl compounds.
4. One of the carbonyl compounds produced is 2-ethylbutanal.
5. The 2-ethylbutanal can undergo oxidation with potassium permanganate (KMnO4) or chromium trioxide (CrO3) in acidic or basic conditions, resulting in the formation of 2-ethylbutanoic acid.
6. Hydrolysis of 2-ethylbutanoic acid can be achieved by reacting it with water, breaking the ester bond and releasing ethanol and the corresponding carboxylic acid.
7. Finally, carbon dioxide (CO2) can be liberated upon heating the carboxylic acid.
c) To synthesize 2-chloro-2-methylpentane and 3-chloro-2-methylpentane from 2-methyl-2-pentene, you would need to perform a substitution reaction known as chlorination. Here are the steps:
1. Start with 2-methyl-2-pentene.
2. React it with a chlorinating agent, such as hydrogen chloride (HCl), in the presence of a Lewis acid catalyst like aluminum chloride (AlCl3).
3. The double bond of 2-methyl-2-pentene will react with HCl, leading to the formation of a carbocation intermediate.
4. This carbocation intermediate can be attacked by chloride ions, resulting in the formation of 2-chloro-2-methylpentane.
5. However, if the chlorine ion attacks the carbocation at a different position, it can yield 3-chloro-2-methylpentane as an alternative product.
d) To synthesize 1-ethyl-1-hydroxy-2-chlorocyclohexane, 1-ethyl-1-chloro-2-hydroxycyclohexane, and 1-ethyl-1,2-dichlorocyclohexane from 1-ethylcyclohexene, you would need to perform substitution reactions. Here are the steps:
1. Start with 1-ethylcyclohexene.
2. React it with a chlorinating agent, such as chlorine gas (Cl2), in the presence of a radical initiator like benzoyl peroxide (BPO).
3. The double bond of 1-ethylcyclohexene will react with chlorine, resulting in the formation of a radical intermediate.
4. This radical intermediate can undergo substitution reactions with chlorine atoms, leading to the formation of 1-ethyl-1-hydroxy-2-chlorocyclohexane, 1-ethyl-1-chloro-2-hydroxycyclohexane, and 1-ethyl-1,2-dichlorocyclohexane.
Keep in mind that the exact conditions and reagents used may vary, and it's always important to have a good understanding of the specific reaction mechanism and conditions for each synthesis.