Concept explainers
(a)
Interpretation:
The product of the reaction of dibutyl sulfide with 1 equivalent of H2O2 at 25 °C is to be predicated.
Concept introduction:
Hydrogen perioxide (H2O2) is an strong oxidizing agent. It is used in many organic synthese to produced oxidized products.
Sulfur containing organic compounds has many similar chemical properties as oxygen contain compound such as ether and aclcohol.
Answer to Problem 11.45AP
The product of the reaction of dibutyl sulfide with 1 equivalent of H2O2 at 25 °C is shown below.
Explanation of Solution
The dibutyl sulfide undergoes an oxidation reaction with hydrogen peroxide. The dibutyl sulfide reacts with 1 equivalent of H2O2 at 25 °C to form a oxidation product dibutyl sulfoxide.
The corresponding
Figure 1
The product of the reaction of dibutyl sulfide with 1 equivalent of H2O2 at 25 °C is shown in Figure 1.
(b)
Interpretation:
The product of the reaction of dibutyl sulfide with 2 or more equivalents of H2O2 and heat is to be predicated.
Concept introduction:
Hydrogen perioxide (H2O2) is an strong oxidizing agent. It is used in many organic synthese to produced oxidized products.
Sulfur containing organic compounds has many similar chemical properties as oxygen contain compound such as ether and aclcohol.
Answer to Problem 11.45AP
The product of the reaction of dibutyl sulfide with 2 or more equivalents of H2O2 and heat shown below.
Explanation of Solution
The dibutyl sulfide undergoes an oxidation reaction with hydrogen peroxide. The dibutyl sulfide reacts with H2O2 to form a oxidation product dibutyl sulfoxide. The dibutyl sulfoxide further oxides to form dibutyl sulfone.
The corresponding chemical reaction is shown below.
Figure 2
The product of the reaction of dibutyl sulfide with 2 or more equivalents of H2O2 and heat shown in Figure 2.
(c)
Interpretation:
The product of the reaction of cis-3-hexene with magnesium monoperoxyphthalate (MMPP) is to be predicated.
Concept introduction:
The magnesium monoperoxyphthalate (MMPP) is an strong oxidizing agent. It is used in many organic synthese to produced oxidized products. It can oxides
Answer to Problem 11.45AP
The product of the reaction of cis-3-hexene with magnesium monoperoxyphthalate (MMPP) is shown below.
Explanation of Solution
The compound cis-3-hexene undergoes a oxidation reaction with magnesium monoperoxyphthalate (MMPP). The magnesium monoperoxyphthalate coverts the alkene into epoxide.
The corresponding chemical reaction is shown below.
Figure 3
The product of the reaction of cis-3-hexene with magnesium monoperoxyphthalate (MMPP) is shown in Figure 3.
(d)
Interpretation:
The product of the reaction of given compound with (CH3)2CuCNLi2 followed by the addition of H3O+ is to be predicated.
Concept introduction:
Epoxides undergo nucleophilic ring-opening reactions which are acid-catalyzed. If the epoxide is unsymmetrical, then the anionic nucleophile will attack the less-hindered carbon atom of the ring. If the reaction conditions are acidic, then the reaction will occur at the more substituted carbon atom.
Answer to Problem 11.45AP
The product of the reaction of given compound with (CH3)2CuCNLi2 followed by the addition of H3O+ is shown below.
Explanation of Solution
The epoxide undergoes ring-opening reaction in the presence of acid. The dilithium dimethylcyanocuprate molecule generates a nucleophile (−CH3). This nucleophile will attack the more substituted carbon atom of the epoxide ring to from the product. The corresponding chemical reaction is shown below.
Figure 4
The product of the reaction of given compound with (CH3)2CuCNLi2 followed by the addition of H3O+ is shown in Figure 4.
(e)
Interpretation:
The product of the reaction of given compound with solvent H2O in acidic solution is to be predicated.
Concept introduction:
Epoxides undergo nucleophilic ring-opening reactions which are acid-catalyzed. If the epoxide is unsymmetrical, then the anionic nucleophile will attack the less-hindered carbon atom of the ring. If the reaction conditions are acidic, then the reaction will occur at the more substituted carbon atom.
Answer to Problem 11.45AP
The product of the reaction of given compound with solvent H2O in acidic solution is shown below.
Explanation of Solution
The epoxide undergoes ring opening reaction in the presence of acid. The water molecule acts a nucleophile and attacks on the more substituted carbon atom of the epoxide ring to from
Figure 5
The product of the reaction of given compound with solvent H2O in acidic solution is shown in Figure 5.
(f)
Interpretation:
The product of the reaction of given compound with periodic acid is to be predicated.
Concept introduction:
The periodic acid acts as a strong oxidizing agent. The periodic acid reacts with a vicinal diol to form two
Answer to Problem 11.45AP
The product of the reaction of given compound with periodic acid is shown below.
Explanation of Solution
The given compound is vicinal diol. It reacts with periodic acid to form two aldehydes. The carbon-carbon bond between the carbon atoms attached to two adjacent hydroxyl groups gets breaks. The corresponding chemical reaction is shown below.
Figure 6
The product of the reaction of given compound with periodic acid is shown in Figure 6.
(g)
Interpretation:
The product of the reaction of given compound with NaH in THF followed by CH3I is to be predicated.
Concept introduction:
The metal hydride reagents are good reducing agents such as NaH. Sodium hydride is used in many organic syntheses as a reducing agent. Sodium hydride can also be used as a base in the organic syntheses reactions. It abstracts the acidic proton from the organic compounds.
Answer to Problem 11.45AP
The product of the reaction of given compound with NaH in THF followed by CH3I is shown below.
Explanation of Solution
The base NaH abstract the proton of the hydroxyl group of alcohol to form an anion. The anion acts as nucleophile and attacks on the carbon atom of CH3I. The corresponding chemical reaction is shown below.
Figure 7
The product of the reaction of given compound with NaH in THF followed by CH3I is shown in Figure 7.
(h)
Interpretation:
The product of the reaction of (E)-3-methyl-3-hexene with Hg(OAc)2 in ethanol solvent followed by NaBH4 is to be predicated.
Concept introduction:
Oxymercuration reaction is a type of reaction in which an alkene get converted into an alcohol. The mercuric acetate is used in the reaction as reagent. This reagent attacks the alkene to form a cyclic intermediate compound which further undergoes reduction to form alcohol.
Answer to Problem 11.45AP
The product of the reaction of (E)-3-methyl-3-hexene with Hg(OAc)2 in ethanol solvent followed by NaBH4 is shown below.
Explanation of Solution
The mercuric acetate Hg(OAc)2 in ethanol solvent reacts with (E)-3-methyl-3-hexene to from a intermediate product which is reduced by the addition of NaBH4 in the reaction mixture. The end product formed in the reaction is an ether due to the use of ethanol as solvent.
The corresponding chemical reaction is shown below.
Figure 8
The product of the reaction of (E)-3-methyl-3-hexene with Hg(OAc)2 in ethanol solvent followed by NaBH4 is shown in Figure 8.
(i)
Interpretation:
The product of the reaction of the given compound with acidic methanol is to be predicated.
Concept introduction:
The replacement or substitution of one
Answer to Problem 11.45AP
The product of the reaction of the given compound with acidic methanol is shown below.
Explanation of Solution
The proton of the acid will protionate the ether. The protonated ether will increase the electrophilic characters of carbon atom attached to the oxygen atom. The methonal can acts as nuclephile, however the nucleophilic charater of methoxy-group and ethoxy group is similar. Therefore, no further reaction will take place.
The corresponding chemical reaction is shown below.
Figure 9
The product of the reaction of the given compound with acidic methanol is shown in Figure 9.
(j)
Interpretation:
The product of the reaction of (R)-3-Methyl-1-bromopentane with Mg in ether followed by addition of ethylene oxide, then with CH3I is to be predicated.
Concept introduction:
Grignard reagents are
Answer to Problem 11.45AP
The product of the reaction of (R)-3-Methyl-1-bromopentane with Mg in ether followed by addition of ethylene oxide, then with CH3I is shown below.
Explanation of Solution
The alkyl halide will react with magnisum metal to from gridnard reagent. These Grignard reagent reacts with epoixde to form alcohol. The alcohol reacts with CH3I to form ether.
The corresponding chemical reaction is shown below.
Figure 10
The product of the reaction of (R)-3-Methyl-1-bromopentane with Mg in ether followed by addition of ethylene oxide, then with CH3I is shown in Figure 10.
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Chapter 11 Solutions
Organic Chemistry
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