Interpretation:
The product of the reaction when the given nitrone undergoes intramolecular
cycloaddition is to be determined.
Concept introduction:
One of them is positively charged while the other is negatively charged.
This dipole acts as a
electron component via the
The
electron component can also be an alkyne which changes to an alkene upon addition.
The resultant structure contains a new five membered ring consisting of the
attached to the two atoms of the alkyne.
The double bond between the carbon atoms of the alkene changes to a single bond.
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Organic Chemistry (Binghampton University)
- Diels–Alder reaction of a monosubstituted diene (such as CH2=CH–CH=CHOCH3) with a monosubstituted dienophile (such as CH2=CHCHO)gives a mixture of products, but the 1,2-disubstituted product oftenpredominates. Draw the resonance hybrid for each reactant, and use thecharge distribution of the hybrids to explain why the 1,2-disubstitutedproduct is the major product.arrow_forwardExamine each of the following ALLOWED electrocyclic, sigmatropic or cycloaddition reactions. Determine in each of these how many electrons are involved. For electrocyclic and cycloaddition reaction, this includes π-electrons (4n or 4n+2); for sigmatropic reactions, one σ bond electrons also contribures. Tell what type of concerted reaction each is, and whether 4n or 4n+2 system. Thank you!arrow_forwardThe compound below is treated with chlorine in the presence of light. CH3 CH,CHCH3 Draw the structure for the organic radical species produced by reaction of the compound with a chlorine atom. Assume reaction occurs at the weakest C-H bond. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms.arrow_forward
- As you might suspect, B-carotene, C,Hw precursor to vitamin A, was first isolated from carrots. Dilute solutions of B-carotene are yellow, hence its use as a food coloring. In plants, it is almost always present in combination with chlorophyll to assist in the harvesting of the energy of sunlight and to protect the plant against reactive species produced in photo- synthesis. As tree leaves die in the fall, the green of their chlorophyll molecules is replaced by the yellows and reds of carotene and carotene-related molecules. Compare the carbon skeletons of B-carotene and lycopene. What are the similarities? What are the differences? H3C. H3C CH3 CH3 CH3 H,C CH3 CH3 CH3 B-Carotenearrow_forwardOrganotin compounds play a significant role in diverse industrial applications. They have been used as plastic stabilizers and as pesticides or fungicides.One method used to prepare simple tetraalkylstannanes is the controlled direct reaction of liquid tin(IV) chloride with highly reactive trialkylaluminum compounds, such as liquid triethylaluminum (Al(C2H5)3). 3SnCl4 + 4Al(C2H5)3 3Sn(C2H5)4 + 4AlCl3 In one experiment, 0.230 L of SnCl4 (d = 2.226 g/mL) was treated with 0.396 L of triethylaluminum (Al(C2H5)3); d = 0.835 g/mL). If 0.335 L of tetraethylstannane (d = 1.187 g/mL) were actually isolated in this experiment, what was the percent yield?arrow_forward1)Chemistry students are taking an experimental course in organic chemistry at a public university. During an experiment involving conjugated dienes, some doubts arose when discussing the results obtained so far: (a) A student obtained two products from the reaction of 1,3-cyclohexadiene with Br2. His lab partner was surprised to get only one product from the reaction of 1,3 - cyclohexadiene with HBr. Explain these distinct results. (b) One student, seeing the discussion of colleagues, commented that she obtained two distinct products when reacting 1,3,5-hexatriene with HBr, with different yields just by changing the reaction temperature. Explain the results she obtained using reaction mechanism and based on kinetic and thermodynamic control involving conjugated dienes.arrow_forward
- Organotin compounds play a significant role in diverse industrial applications. They have been used as plastic stabilizers and as pesticides or fungicides. One method used to prepare simple tetraalkylstannanes is the controlled direct reaction of liquid tin(IV) chloride with highly reactive trialkylaluminum compounds, such as liquid triethylaluminum (Al(CzHs)3). 3SnCl4 + 4Al(C2H5)3 → 3Sn(C2H5)4 + 4AlCl3 In one experiment, 0.160 L of SnCl4 (d= 2.226 g/mL) was treated with 0.346 L of triethylaluminum (Al(C2H5)3); d = 0.835 g/mL). What is the theoretical yield in this experiment (mass of tetraethylstannane, Sn(C2H5)4)? If 0.257L of tetraethylstannane (d= 1.187 g/mL) were actually isolated in this experiment, what was the percent yield?arrow_forwardShow that the [4 + 4] cycloaddition of two butadiene molecules to give cycloocta1,5-diene is thermally forbidden but photochemically allowedarrow_forwardMechanism The Diels-Alder reaction is part of a class of reactions known as a cycloaddition reaction. This reaction is specifically a [4+2] cycloaddition which is a concerted (one-step) process in which two new carbon - carbon sigma bonds are formed from two pi bonds. For the first Diels - Alder step of the mechanism fill in the arrows needed for the transformation. The rest of the mechanism is drawn for you. OH Show mechanism arrows for this step! 4 + 2 cycloaddition OH H D- & H+ transfer OH Nuc acyl substitution H L.G.arrow_forward
- Under certain conditions, 1,3-butadiene can function as both a diene and a dienophile. Draw a structural formula for the Diels-Alder adduct formed by reaction of 1,3-butadiene with itself.arrow_forwardPredict the products for the hydrohalogenation reaction of 1-methyl-1,3-cyclohexadiene with 1 equivalent of HBr in thermodynamic conditions.arrow_forwardQ3. 1. What is meant of 1,2-adduct and 1,4-adduct for the reaction of 1,3-butadiene with hydrobromic acid, writes the reaction? b. What is the one requirement for the diene of a Diels-Alder reaction?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning