Problem 49 - Chemistry An Atoms First Approach

Question

Mimosine is a natural product found in large quantities in the seeds and foliage of some legume plants and has been shown to cause inhibition of hair growth and hair loss in mice. a. What functional groups are present in mimosine? b. Give the hybridization of the eight carbon atoms in mimosine. c. How many \(\sigma\) and \(\pi\) bonds are found in mimosine?

Step-by-Step Solution

Answer

Mimosine contains 4 distinct functional groups: amino group, carboxyl group, hydroxyl group, and pyridone ring. There are five sp^3 hybridized carbon atoms (C5, C6, C7, and C8) and three sp^2 hybridized carbon atoms (C1, C2, C3, and C4) in mimosine. In total, mimosine has 19 σ bonds and 3 π bonds.

Step 1: Determine the Structure of Mimosine

First, let's look at the structure of mimosine. Mimosine has the chemical formula C_8H_10N_2O_4 with the following structure: 

Step 2: Identify Functional Groups

Now that we have the structure, let's identify the functional groups present in mimosine: 1. Amino group (-NH_2) 2. Carboxyl group (-COOH) 3. Hydroxyl group (-OH) 4. Pyridone ring (a 6-membered aromatic ring with a nitrogen atom and a carbonyl group) Mimosine contains 4 distinct functional groups: amino group, carboxyl group, hydroxyl group, and pyridone ring. #b. Hybridization of the eight carbon atoms in mimosine#

Step 3: Identify Hybridization of Carbon Atoms

Now, let's determine the hybridization of all eight carbon atoms in mimosine: 1. The carbon atom in the carboxyl group (C1) is sp^2 hybridized. 2. The three carbon atoms in the pyridone ring (C2, C3, and C4) are also sp^2 hybridized. 3. The carbon atom bonded to the amino group (C5) is sp^3 hybridized. 4. The carbon atom bonded to the hydroxyl group (C6) is sp^3 hybridized. 5. The two remaining carbon atoms (C7 and C8) in the alkyl chain are also sp^3 hybridized. In summary, there are five sp^3 hybridized carbon atoms (C5, C6, C7, and C8) and three sp^2 hybridized carbon atoms (C1, C2, C3, and C4) in mimosine. #c. Count σ and π bonds in mimosine#

Step 4: Count σ bonds

First, let's count the number of σ bonds in mimosine. Remember that every single bond is a σ bond: 1. There are 7 single bonds between the carbon atoms (C1-C2, C2-C3, C3-C4, C5-C6, C6-C7, C7-C8, and C8-C5). 2. There are 3 single bonds between the carbon and oxygen atoms (C1-O, C4=O, and C6-O). 3. There is 1 single bond between the carbon and nitrogen atoms (C5-N). 4. There are 8 single bonds between carbon and hydrogen atoms. In total, there are 19 σ bonds in mimosine.

Step 5: Count π bonds

Now let's count the π bonds in mimosine: 1. There are 2 π bonds in the pyridone ring (C2=C3 and C4=C1). 2. There is 1 π bond in the carbonyl group (C4=O). In total, there are 3 π bonds in mimosine. Finally, we can conclude that mimosine has 19 σ bonds and 3 π bonds.