Concept explainers
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(a)
Interpretation:
The carbonyl carbon and phosphonium ylide that are needed to synthesize the given compound has to be identified.
Concept introduction:
Wittig reaction:
Witting reaction is the reaction between the carbonyl carbon of
Specific phosphonium ylide can be prepared for specific alkene synthesis. The triphenylphosphine is reacted with
The mechanism of the witting reaction is:
(b)
Interpretation:
The carbonyl carbon and phosphonium ylide that are needed to synthesize the given compound has to be identified.
Concept introduction:
Wittig reaction:
Witting reaction is the reaction between the carbonyl carbon of aldehyde or ketone and the phosphonium ylide to give an alkene. Wittig reaction is a very useful method to synthesize the compound which can’t be synthesis easily by other methods.
Specific phosphonium ylide can be prepared for specific alkene synthesis. The triphenylphosphine is reacted with alkyl halide that has required numbers of carbon. A strong base such as sodium hydride or butyllithium is added to remove proton of carbon adjacent to the phosphorus atom. The carbon of prepared phosphonium ylide have nucleophilic character and get attached to the carbonyl carbon and carbonyl oxygen get attached to the positively charged phosphorous. Triphenylphosphine oxide gets eliminated resulting in the formation of the alkene.
The mechanism of the witting reaction is:
(c)
Interpretation:
The carbonyl carbon and phosphonium ylide that are needed to synthesize the given compound has to be identified.
Concept introduction:
Wittig reaction:
Witting reaction is the reaction between the carbonyl carbon of aldehyde or ketone and the phosphonium ylide to give an alkene. Wittig reaction is a very useful method to synthesize the compound which can’t be synthesis easily by other methods.
Specific phosphonium ylide can be prepared for specific alkene synthesis. The triphenylphosphine is reacted with alkyl halide that has required numbers of carbon. A strong base such as sodium hydride or butyllithium is added to remove proton of carbon adjacent to the phosphorus atom. The carbon of prepared phosphonium ylide have nucleophilic character and get attached to the carbonyl carbon and carbonyl oxygen get attached to the positively charged phosphorous. Triphenylphosphine oxide gets eliminated resulting in the formation of the alkene.
The mechanism of the witting reaction is:
(d)
Interpretation:
The carbonyl carbon and phosphonium ylide that are needed to synthesize the given compound has to be identified.
Concept introduction:
Wittig reaction:
Witting reaction is the reaction between the carbonyl carbon of aldehyde or ketone and the phosphonium ylide to give an alkene. Wittig reaction is a very useful method to synthesize the compound which can’t be synthesis easily by other methods.
Specific phosphonium ylide can be prepared for specific alkene synthesis. The triphenylphosphine is reacted with alkyl halide that has required numbers of carbon. A strong base such as sodium hydride or butyllithium is added to remove proton of carbon adjacent to the phosphorus atom. The carbon of prepared phosphonium ylide have nucleophilic character and get attached to the carbonyl carbon and carbonyl oxygen get attached to the positively charged phosphorous. Triphenylphosphine oxide gets eliminated resulting in the formation of the alkene.
The mechanism of the witting reaction is:
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Chapter 16 Solutions
Organic Chemistry, Books a la Carte Edition (8th Edition)
- 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
- give example for the following(by equation) a. Converting a water insoluble compound to a soluble one. b. Diazotization reaction form diazonium salt c. coupling reaction of a diazonium salt d. indacator properties of MO e. Diazotization ( diazonium salt of bromobenzene)arrow_forward2-Propanone and ethyllithium are mixed and subsequently acid hydrolyzed. Draw and name the structures of the products.arrow_forward(Methanesulfinyl)methane is reacted with NaH, and then with acetophenone. Draw and name the structures of the products.arrow_forward
- 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
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning