a)
Interpretation:
Whether the mechanism of the reaction given is polar, radical or both to be identified.
Concept introduction:
A polar mechanism involves the formation of carbocation or carbanion as intermediates. A radical mechanism involves the free radicals as intermediates.
To identify:
Whether the mechanism of the reaction given is polar, radical or both.
b)
Interpretation:
Whether the mechanism of the reaction given is polar, radical or both to be identified.
Concept introduction:
A polar mechanism involves the formation of carbocation or carbanion as intermediates. A radical mechanism involves the free radicals as intermediates.
To identify:
Whether the mechanism of the reaction given is polar, radical or both.
c)
Interpretation:
Whether the mechanism of the reaction given is polar, radical or both to be identified.
Concept introduction:
A polar mechanism involves the formation of carbocation or carbanion as intermediates. A radical mechanism involves the free radicals as intermediates.
To identify:
Whether the mechanism of the reaction given is polar, radical or both.
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Chapter 9 Solutions
Organic Chemistry
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- In the presence of a radical initiator (Z•), tributyltin hydride (R3SnH, R = CH3CH2CH2CH2) reduces alkyl halides to alkanes: R′X + R3SnH → R′H + R3SnX. The mechanism consists of a radical chain process with an intermediate tin radical: This reaction has been employed in many radical cyclization reactions. Draw a stepwise mechanism for the following reaction.arrow_forwardMethyl bromide is widely used as a fumigant to prevent the spread of diseases and pests in agricultural products, and it can be prepared from methane via radical bromination. Recently, a new method for preparing methyl bromide was developed, involving genetically engineered microorganisms that are capable of producing large quantities of the compound. Draw a mechanism for the radical bromination of methane to yield bromomethane. Draw the first step of the mechanism (initiation stage). Include all nonbonded electrons (lone pairs and radicals) in your answer. Edit Drawing eTextbook and Media Draw the second step of the mechanism (propagation stage). Include all nonbonded electrons (lone pairs and radicals) in your answer. * Edit Drawing Draw the third step of the mechanism (propagation stage). Include all nonbonded electrons (lone pairs and radicals) in your answer. * Edit Drawing In practice, radical bromination of methane produces many by-products. For example, ethane is obtained in…arrow_forwardFill both dashes in the paragraph 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 (discussed in the lecture videos) containing a phenol group with antioxidant properties is: ---------.arrow_forward
- When exactly 1 mole of methane is mixed with exactly 1 mole of chlorine and light is shone on the mixture, a chlorination reaction occurs. The products are found to contain substantial amounts of di-, tri-, and tetrachloromethane, as well as unreacted methane. Explain how a mixture is formed from this stoichiometric mixture of reactants, and propose mechanisms for the formation of these compounds from chloromethane.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_forwardAll electrophilic aromatic substitution reactions occur via a two-step mechanism: addition of the electrophile to form a resonance-stabilized carbocation, followed by deprotonation by a base. In the step shown below, loss of a proton to form the substitution product was drawn using the resonance structure with the + 1 formal charge at the ortho position to the carbon bonded to the electrophile. Redraw the step shown with the other two resonance structures and use curved arrows to show how these other two resonance structures can be converted to the substitution product by removal of a proton with the base shown. Part: 0/2 Part 1 of 2 H :CI-AICI, Draw the mechanism that generates the final substitution product with the +1 formal charge at the para position. Cl HC1 AICI3arrow_forward
- Chemistry Glutathione (or GSH) can form a disulfide bridge with another glutathione molecule via radical reaction. Show a mechanism of a hydroxide radical reacting with two glutathione molecules to a produce a dimer (GSSG).arrow_forwardTributyltin hydride (Bu3SnH) is used synthetically to reduce alkyl halides, replacing a halogen atom with hydrogen. Free-radical initiators promote this reaction, and free-radical inhibitors are known to slow or stop it. Your job is todevelop a mechanism,arrow_forwardDraw the structure of either vitamin C or vitamin E and show how they interact with a radical species. Explain briefly why they are good antioxidants.arrow_forward
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