a)
Interpretation:
To predict the product of the reaction shown with regiochemistry, if relevant.
Concept introduction:
Catalytic hydrogenation is a heterogeneous process which occurs with syn stereochemistry. Both hydrogens adsorbed on the catalytic surface add to the double bond from the same face.
To predict:
The product of the reaction shown with regiochemistry, if relevant.
Answer to Problem 42AP
The product of the reaction is ethylbenzene.
Explanation of Solution
The addition of hydrogen takes place to the double bond in the side chain with syn stereochemistry. Both hydrogens add to the double bond from the same face to yield ethylbenzene.
The product of the reaction is ethylbenzene.
b)
Interpretation:
To predict the product of the reaction shown with regiochemistry, if relevant.
Concept introduction:
Addition of bromine to the double bond in
To predict:
The product of the reaction shown with regiochemistry, if relevant.
Answer to Problem 42AP
The product of the reaction is
Explanation of Solution
In the first step the addition of bromine to the double bond in 1,2-dimethylcyclohexane results in the formation of a cyclic bromonium ion with the simultaneous elimination of a bromide ion. The large bromonium ion shields one side of the molecule. Hence the attack of the bromide ion occurs from the opposite, unshielded side to yield a trans-product.
The product of the reaction is
c)
Interpretation:
To predict the product of the reaction shown with regiochemistry, if relevant.
Concept introduction:
Hydroxylation of double bonds can be carried out directly by treating the alkene with osmium tetroxide, OsO4, in the presence of N-phenylmorpholine N-oxide. The reaction occurs with syn stereochemistry through the formation of a cyclic intermediate, called osmate, formed by the addition of OsO4 to the alkene in a single step. The cyclic osmate is then cleaved to give the cis-1,2-
To predict:
The product of the reaction shown with regiochemistry, if relevant.
Answer to Problem 42AP
The product of the reaction is
Explanation of Solution
OsO4 adds to the double bond in the side chain from the same side to yield a cyclic osmate in a single step. When treated with NaHSO3 the cyclic osmate gets cleaved to give the diol.
The product of the reaction is
d)
Interpretation:
To predict the product of the reaction shown with regiochemistry, if relevant.
Concept introduction:
The addition of chlorine to alkenes in the presence of water results in the anti addition of the halohydrin, HOCl, to the double bond. In the first step a cyclic chloronium ion is formed by the attack of the π electrons of the double bond on chlorine. In the second step water attacks the chloronium ion from the least shielded side to give an anti addition product. The addition obeys Markovnokov orientation. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents.
To predict:
The product of the reaction shown with regiochemistry, if relevant.
Answer to Problem 42AP
The product of the reaction is
Explanation of Solution
The given alkene has an unsymmetrically substituted double bond in the side chain. In the first step a cyclic chloronium ion is formed by the attack of the double bond on chlorine. In the second step water attacks the the chloronium ion from the opposite less shielded side to give an intermediate which then loses a proton to yield the product.
The product of the reaction is
e)
Interpretation:
The product expected in the reaction shown is to be given.
Concept introduction:
The reaction given is an example of Simmons-Smith reaction. When CH2I2 is treated with Zn/Cu couple, iodomethylzinc iodide, ICH2ZnI, is formed. This ICH2ZnI transfers a CH2 group to the double bond in alkene to form a cyclopropane ring in the product.
To give:
The product expected in the reaction shown.
Answer to Problem 42AP
The product expected in the reaction shown is
Explanation of Solution
When CH2I2 is treated with Zn/Cu couple, iodomethylzinc iodide, ICH2ZnI, is formed. This ICH2ZnI transfers a CH2 group to the double bond in the side chain to form a cyclopropane ring in the product.
The product expected in the reaction shown is
f)
Interpretation:
The product expected in the reaction shown is to be given.
Concept introduction:
Alkenes are oxidized to give
To give:
The product expected in the reaction shown.
Answer to Problem 42AP
The product expected in the reaction shown is
Where RCO3H = meta-chloroperoxybenzoic acid
Explanation of Solution
The oxygen transfer from the peroxy acids to the double bond in the side chain takes place with syn stereochemistry. Both the C-O bonds are formed from the same face of the double bond through a one step process without the formation of an intermediate to yield the product.
The product expected in the reaction shown is
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Chapter 8 Solutions
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- For each reaction below, decide if the first stable organic product that forms in solution will create a new CC bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. དྲ。 ✗MgBr ? O CI Will the first product that forms in this reaction create a new C-C bond? Yes No • ? Will the first product that forms in this reaction create a new CC bond? Yes No × : ☐ Xarrow_forwardPredict the major products of this organic reaction: OH NaBH4 H ? CH3OH Note: be sure you use dash and wedge bonds when necessary, for example to distinguish between major products with different stereochemistry. Click and drag to start drawing a structure. ☐ : Sarrow_forwardPredict the major products of this organic reaction: 1. LIAIHA 2. H₂O ? Note: be sure you use dash and wedge bonds when necessary, for example to distinguish between major products with different stereochemistry. Click and drag to start drawing a structure. X : ☐arrow_forward
- For each reaction below, decide if the first stable organic product that forms in solution will create a new C - C bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. NH2 tu ? ? OH Will the first product that forms in this reaction create a new CC bond? Yes No Will the first product that forms in this reaction create a new CC bond? Yes No C $ ©arrow_forwardAs the lead product manager at OrganometALEKS Industries, you are trying to decide if the following reaction will make a molecule with a new C-C bond as its major product: 1. MgCl ? 2. H₂O* If this reaction will work, draw the major organic product or products you would expect in the drawing area below. If there's more than one major product, you can draw them in any arrangement you like. Be sure you use wedge and dash bonds if necessary, for example to distinguish between major products with different stereochemistry. If the major products of this reaction won't have a new CC bond, just check the box under the drawing area and leave it blank. Click and drag to start drawing a structure. This reaction will not make a product with a new CC bond. G marrow_forwardIncluding activity coefficients, find [Hg22+] in saturated Hg2Br2 in 0.00100 M NH4 Ksp Hg2Br2 = 5.6×10-23.arrow_forward
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- 3-Oxo-butanenitrile and (E)-2-butenal are mixed with sodium ethoxide in ethanol. Draw and name the structures of the products.arrow_forwardWhat is the reason of the following(use equations if possible) a.) In MO preperation through diazotization: Addition of sodium nitrite in acidfied solution in order to form diazonium salt b.) in MO experiment: addition of sodium hydroxide solution in the last step to isolate the product MO. What is the color of MO at low pH c.) In MO experiment: addition of sodium hydroxide solution in the last step to isolate the product MO. What is the color of MO at pH 4.5 d.) Avoiding not cooling down the reaction mixture when preparing the diazonium salt e.) Cbvcarrow_forwardA 0.552-g sample of an unknown acid was dissolved in water to a total volume of 20.0 mL. This sample was titrated with 0.1103 M KOH. The equivalence point occurred at 29.42 mL base added. The pH of the solution at 10.0 mL base added was 3.72. Determine the molar mass of the acid. Determine the Ka of the acid.arrow_forward
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