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Draw enol tautomer(s) for each compound. Ignore stereoisomers.
(a)
Interpretation: Enol tautomer(s) of the given compound is to be drawn.
Concept introduction: Tautomers are the isomers which differ only in the position of the hydrogens and electrons of electronegative element, generally oxygen. There is no change in the carbon skeleton of the compound. This phenomenon which involves simple proton transfer in an intramolecular fashion is known as tautomerism.
The very common example of tautomerism is Keto-enol tautomerism. It can be acid or base catalysed.
Answer to Problem 30P
. The enol tautomer of this compound is shown below:
Explanation of Solution
Tautomers are isomers which differ only in the position of the protons and electrons of the compound. There is no change in the carbon skeleton of the compound. The ball and stick model as shown in Figure 1.
Figure 1
The enol tautomer of this compound is shown in Figure 2.
Figure 2
The tautomer of the given compound is showed in Figure 2.
(b)
Interpretation: Enol tautomer(s) of the given compound is to be drawn.
Concept introduction:
Tautomers are the isomers which differ only in the position of the hydrogens and electrons of electronegative element, generally oxygen. There is no change in the carbon skeleton of the compound. This phenomenon which involves simple proton transfer in an intramolecular fashion is known as tautomerism.
The very common example of tautomerism is Keto-enol tautomerism. It can be acid or base catalysed.
Answer to Problem 30P
. The enol tautomer of this compound is shown below:
Explanation of Solution
Tautomers are isomers which differ only in the position of the protons and electrons of the compound. There is no change in the carbon skeleton of the compound. The ball and stick model as shown in Figure 3.
Figure 3
The enol tautomer of this compound is shown in Figure 4.
Figure 4
The tautomer of the given compound is showed in Figure 4.
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Chapter 21 Solutions
ORGANIC CHEMISTRY BOOK& SG/SM
- Convert each compound to its enol or keto tautomer.arrow_forwardSynthesize each compound from cyclohexanol using any other organic or inorganic compounds. CH,OH a. g. (Each cyclohexane ring must come from cyclohexanol.) COOH b. d. h. сно CHs (Each cyclohexane ring must come from cyclohexanol.)arrow_forwardDraw the enol or keto tautomer(s) of each compound.arrow_forward
- Answer the following questions about curcumin, a yellow pigment isolated from turmeric, a tropical perennial in the ginger family and a principal ingredient in curry powder.a.In Chapter 11, we learned that most enols, compounds that contain a hydroxy group bonded to a C=C, are unstable and tautomerize to carbonyl groups. Draw the keto form of the enol of curcumin, and explain why the enol is more stable than many other enols. b.Explain why the enol O—H proton is more acidic than an alcohol O—H proton. c. Why is curcumin colored? d.Explain why curcumin is an antioxidant.arrow_forwardSynthesize each compound from cyclohexanol, ethanol, and any other needed reagents.arrow_forwardDraw the products formed when A or B is treated with each reagent. In some cases, no reaction occurs.a. NaBH4, CH3OHb. [1] LiAlH4; [2] H2Oc. [1] CH3MgBr (excess); [2] H2Od. [1] C6H5Li (excess); [2] H2Oe. Na2Cr2O7, H2SO4, H2Oarrow_forward
- Label each pair of compounds as keto–enol tautomers or constitutional isomers, but not tautomers.arrow_forwardDraw a stepwise mechanism for the following substitution. Explain why 2-chloropyridine reacts faster than chlorobenzene in this type of reaction.arrow_forwardDraw a stepwise mechanism for the following substitution. Explain why 2-chloropyridine reacts faster than chlorobenzene in this type of reaction.arrow_forward
- Draw enol tautomer(s) for each attached compound ?arrow_forwardDraw a stepwise mechanism for the following reaction.arrow_forwardTwo naturally occurring compounds that contain stable cyclic hemiacetals and acetals are monensin and digoxin, the chapter-opening molecule. Monensin, a polyether antibiotic produced by Streptomyces cinamonensis, is used as an additive in cattle feed. Digoxin is a widely prescribed cardiac drug used to increase the force of heart contractions. Label each acetal, hemiacetal, and ether in both compounds.arrow_forward
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning