Heating carvone with aqueous sulfuric acid converts it into carvacrol. The mechanism involves the following steps:
1 answer:
Answer:
See figure 1
Explanation:
In this question, we have to start with the <u>protonation of the double bond</u>. In carvone we have two double bonds, so, we have to decide first which one would be protonated.
The problem states that the <u>terminal alkene</u> is the one that would is protonated. Therefore, we have to do the <u>protonation</u> in the double bond at the bottom to produce the <u>carbocation number 1</u>. Then, a hydride shift takes place to produce the <u>carbocation number 2</u>. A continuation, an <u>elimination reaction</u> takes place to produce the <u>conjugated diene</u>. Then the diene is protonated at the <u>carbonyl group</u> and with an elimination reaction of an hydrogen in the <u>alpha carbon</u> we can obtain <u>carvacol. </u>
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Here we have to draw the four isomers of the compound 3-bromo-4-fluorohexane.
The four isomers of the compound is shown in the figure.
In an organic molecule the chiral -C center is that where four (4) different groups are present. In 3-bromo-4-fluorohexane the 3 and 4 positions are chiral centers. The possible isomers of a molecule can be obtained from the formula 2n. As here 2 chiral centers are present thus number of stereoisomers will be 2×2 = 4.
The four different isomers as shown in the figure are 3R-, 4R-; 3S-, 4S; 3R, 4S and 3S-, 4R- 3-bromo-4-fluorohexane.
In the 3-bromo-4-fluorohexane the functional groups are -Br, C₂H₅, -C₃H₆F and -H for 3-position and -F, -C₂H₅, -C₃H₆ and -H for 4-position respectively.
The priority of the -3 position will be Br > C₃H₆F > C₂H₅ > H and for -4 position F > C₃H₆Br > C₂H₅ > H. If the rotation from the higher priority group to lower is clockwise and anticlockwise then the S- and R- notation are used respectively. However if the -H atom is present at the horizontal position then the notation will be reverse.
Thus the four isomers of the compound is shown.
