Concept explainers
Interpretation:
Among the given pair of compounds, the compound that has the greater enol content is to be identified.
Concept introduction:
Enol refers to an intermediate structure that consists of an
The percentage of enol in keto-enol tautomerism depends upon the stability of enol formed.
Answer to Problem 29P
Solution:
a) Among the given pair of compounds, the second compound has the greater enol content.
b) Among the given pair of compounds, the first compound has the greater enol content.
c) Among the given pair of compounds, the first compound has the greater enol content.
d) Among the given pair of compounds, the first compound has the greater enol content.
Explanation of Solution
a) The compound having higher enol content.
The given pair of compounds is shown below.
The formation of enol occurs when a molecule contains protons on its alpha carbon atom. The extraction of protons takes place from the alpha carbon atom of molecule to form an enol. In the given compounds, the first compound does not possess an alpha proton. Therefore, it does not form an enol. On the other hand, the second compound has alpha proton that can be extracted to form enol. Hence, the second compound has the greater enol content.
b) The compound having higher enol content.
The given pair of compounds is shown below.
The formation of enol occurs when a molecule contains protons on its alpha carbon atom. The extraction of protons takes place from the alpha carbon atom of molecule to form an enol. In the given compounds, the second compound does not possess an alpha proton. Therefore, it does not form an enol. On the other hand, the first compound has alpha proton that can be extracted to form enol. Hence, the first compound has the greater enol content.
c) The compound having higher enol content.
The given pair of compounds is shown below.
The formation of enol occurs when a molecule contains protons on its alpha carbon atom. The extraction of protons takes place from the alpha carbon atom of molecule to form an enol. Both the compounds have alpha protons. In this case, the position of the existing double bond in relation to the new double bond that results when the enol is generated is considered. Their enols are shown below.
The first compound forms a conjugated set of double bonds, whereas in the second compound, the two double bonds are completely isolated. The conjugation refers to a stabilizing characteristic. Therefore, the first compound has the greater enol content.
d) The compound having higher enol content.
The given pair of compounds is shown below.
The formation of enol occurs when a molecule contains protons on its alpha carbon atom. The extraction of protons takes place from the alpha carbon atom of molecule to form an enol. Both the compounds have alpha protons. In this case, the possible resonance forms of the enol are considered. Their enols with resonance forms are shown below.
The first compound contains two oxygen atoms. Both these oxygens carry the negative charge of the enolate that is the intermediate of the enol to keto tautomerization. Therefore, the first compound has the greater enol content.
Want to see more full solutions like this?
Chapter 21 Solutions
Organic Chemistry - Standalone book
- Show how to convert ethyl benzene to (a) 2,5-dichlorobenzoic acid and (b) 2,4-dichlorobenzoic acid.arrow_forwardHelp me solve this problem. Thank you in advance.arrow_forward22.7 Predict the monoalkylated products of the following reactions with benzene. (a) AlCl3 Ya (b) AlCl3 (c) H3PO4 (d) 22.8 Think-Pair-Share AICI3 The reaction below is a common electrophilic aromatic substitution. SO3 H₂SO4 SO₂H (a) Draw the reaction mechanism for this reaction using HSO,+ as the electrophile. (b) Sketch the reaction coordinate diagram, where the product is lower in energy than the starting reactant. (c) Which step in the reaction mechanism is highest in energy? Explain. (d) Which of the following reaction conditions could be used in an electrophilic aro- matic substitution with benzene to provide substituted phenyl derivatives? (i) AICI3 HNO3 H₂SO4 K2Cr2O7 (iii) H₂SO4 (iv) H₂PO₁arrow_forward
- Is an acid-base reaction the only type of reaction that would cause leavening products to rise?arrow_forwardHelp me understand this! Thank you in advance.arrow_forward22.22 For each compound, indicate which group on the ring is more strongly activating and then draw a structural formula of the major product formed by nitration of the compound. Br CHO (a) CH3 (b) (c) CHO CH3 SO₂H (d) ☑ OCHS NO₂ (e) (f) CO₂H NHCOCH3 NHCOCH, (h) CHS 22.23 The following molecules each contain two aromatic rings. (b) 000-100- H3C (a) (c) Which ring in each undergoes electrophilic aromatic substitution more readily? Draw the major product formed on nitration.arrow_forward
- V Consider this step in a radical reaction: Br: ? What type of step is this? Check all that apply. Draw the products of the step on the right-hand side of the drawing area below. If more than one set of products is possible, draw any set. Also, draw the mechanism arrows on the left-hand side of the drawing area to show how this happens. ⚫ionization termination initialization neutralization none of the abc Explanation Check 80 Ο F3 F1 F2 2 F4 01 % do5 $ 94 #3 X 5 C MacBook Air 25 F5 F6 66 ©2025 ˇ F7 29 & 7 8arrow_forwardShow how to convert ethyl benzene to (a) 2,5-dichlorobenzoic acid and (b) 2,4-dichlorobenzoic acid.arrow_forwardno aiarrow_forward
- Polymers may be composed of thousands of monomers. Draw three repeat units (trimer) of the polymer formed in this reaction. Assume there are hydrogen atoms there are hydrogen atoms on the two ends of the trimer. Ignore inorganic byproducts.arrow_forwardDraw a tetramer if this alternating copolymer pleasearrow_forwardDraw the monomers required to synthesize this condensation polymer.arrow_forward
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning