Concept explainers
Interpretation: Reason behind more stability of
Concept introduction:
Aliphatic compound can be described as an organic compound in which carbon and hydrogen atoms are present which are linked together in straight or branched chains.
Free radicals are an uncharged molecule having an unpaired valency electron. These are typically highly reactive and short-lived molecule
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Chapter 9 Solutions
Experimental Organic Chemistry: A Miniscale & Microscale Approach (Cengage Learning Laboratory Series for Organic Chemistry)
- Exp3: Diels-Alder reaction Why does cyclopentadiene regularly form a dimer? How to break the dimer into monomers? Does the diene in this reaction act as the nucleophile or the electrophile? Is the maleic anhydride a nucleophile or an electrophile in this reaction? Explain your reasoning.arrow_forwardWhen a-tocopherol reacts with radicals (such as peroxyl radicals ROO, oxygen radicals, HO), it forms the radical (tocopheroxyl radical) shown below. This radical can eventually be converted back to a- tocopherol with the help of Vitamin C) CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 Draw all resonance contributors of tocopheroxyl radical using the partial drawing shown on the next page. You may NOT need all of the structures.arrow_forwardAre there more than 4 resonance structures?arrow_forward
- 1. In a Birch reaction, an aromatic compound can be treated with Na/CH3OH, it can also be treated with Li/NH3 and have the same product form. One of the intermediates in the Birch reaction is a radical anion. In the example below, anisole could possibly form a radical anion A or B, then will go into C and D. Li/NH3 A B C D A. With the knowledge you have gained from what we have discussed, which anion A or B is more stable? What is your reasoning? B. Is a Birch reaction and oxidation or reduction? Why?arrow_forwardFill the blank space. Compounds containing a phenol group may work as ANTIOXIDANTS to prevent free radical damage. This is accomplished when a free radical (or UV light) encounters a phenol group, turning the phenol group into a radical. However, contrary to typical radical behavior, the structure of the phenol radical can neutralize (or quench) the unpaired electron. Specifically, the phenol structure neutralizes (or quenches) the unpaired radical electron by doing the following: taking the electron and ---------. The correct name (or abbreviation) of an example compound containing a phenol group with antioxidant properties is: ---------.arrow_forwardCompounds containing a phenol group may work as ANTIOXIDANTS to prevent free radical damage. This is accomplished when a free radical (or UV light) encounters a phenol group, turning the phenol group into a radical. However, contrary to typical radical behavior, the structure of the phenol radical can neutralize (or quench) the unpaired electron. Specifically, the phenol structure neutralizes (or quenches) the unpaired radical electron by doing the following: taking the electron and The correct name (or abbreviation) of an example compound (discussed in the lecture videos) containing a phenol group with antioxidant properties is:arrow_forward
- a.What carbon radical is formed by homolysis of the C–Ha bond in propylbenzene? Draw all reasonable resonance structures for this radical. b.What carbon radical is formed by homolysis of the C–Hb bond in propylbenzene? Draw all reasonable resonance structures for this radical. c. The bond dissociation energy of one of the C–H bonds is considerably less than the bond dissociation energy of the other. Which C–H bond is weaker? Offer an explanation.arrow_forwardCompounds P and Q can undergo a Diels-Alder reaction to form two regioisomeric products R and S as shown in Figure 5. OMe O C8H12O2 R C8H12O2 S Figure 5 Draw the chemical structures of regioisomeric compounds R and S. Using possible resonance contributors of P and Q predict which of the two regioisomers will be favoured in the reaction. Using curly arrows, draw the mechanism for the reaction of P and Q to form the dominant regioisomer you have predicted in your answer to part (ii) above.arrow_forwardDraw all resonance structures of the radical that results from abstraction of a hydrogen atom from the antioxidant BHA (butylated hydroxy anisole).arrow_forward
- The compound below is treated with W-bromosuccinimide (NBS) in the presence of light. Draw both resonance structures for the radical produced by reaction of the compound with a bromine atom. Assume reaction occurs only at the weakest C-H bond. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. Separate resonance structures using the ↔ symbol from the drop-down menu. • Include all valence radical electrons in your answer. Y ? #[ ] درarrow_forwardname compoundsarrow_forwardWhich of the following is the most stable carbon radical? O.C(CH3)3 OCH2CH3 O-CH(CH3)2 O.CH3arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning