Question

What is the difference in the Wittig reaction outcome if triethylphosphite is used instead of triphenylphosphine?

What is the difference in the Wittig reaction outcome if triethylphosphite is used instead of triphenylphosphine?

Homework Answers

Answer #1

The difference in the Wittig reaction outcome if triethylphosphite is used instead of triphenylphosphine is that then it is called  Horner–Wadsworth–Emmons reaction (HWE)

The phosphonates used in Horner–Wadsworth–Emmons reaction (HWE) is more reactive than classical Wittig reaction which stabilized ylides when react with ketones and aldehydes.

Another advantage of the Horner–Wadsworth–Emmons reaction (HWE).i.e. when triphenylphosphite is used in the reaction over the classic Wittig reaction which uses triethylphosphine is that the phosphorus byproducts are water-soluble and hence readily separated from the desired product.

Phosphonates which lack a stabilizing a substituent at R2 (for example COO-, COOR, CN, SO2R, vinyl, aryl P(O)(OR)2, OR or NR2) generally result in a low yield of the product alkene.

Know the answer?
Your Answer:

Post as a guest

Your Name:

What's your source?

Earn Coins

Coins can be redeemed for fabulous gifts.

Not the answer you're looking for?
Ask your own homework help question
Similar Questions
The nucleophile in the Wittig reaction is a phosphorous-stabilized carbanion called an ylide. The ylides are...
The nucleophile in the Wittig reaction is a phosphorous-stabilized carbanion called an ylide. The ylides are synthesized by employing a strong base to remove an acidic proton and a halogen from a alkyl triphenylphosphonium halide salt. The alkyl triphenylphosphonium halide salts are made via an SN2 reaction between an appropriate alkyl halide substrate and triphenylphosphine. So we could consider these SN2 reactions as the "first step" in a multi-step Wittig synthesis. Could bromobenzene be a starting material in one of...
6. What is the Wittig reaction. Show the course of the reaction by using triphenylphosphin, methylbromide,...
6. What is the Wittig reaction. Show the course of the reaction by using triphenylphosphin, methylbromide, as a starting materials, PhLi as base and benzaldehyde as the carbonyl component (15 points). Draw all intermediates, products, and special conditions where needed.
In a stereospecific Wittig reaction: Discuss how a carbon nucleophile was generated from benzyltriphenylphosphonium chloride.
In a stereospecific Wittig reaction: Discuss how a carbon nucleophile was generated from benzyltriphenylphosphonium chloride.
Why is paraformaldehyde is used in the Mannich reaction instead of formaldehyde?
Why is paraformaldehyde is used in the Mannich reaction instead of formaldehyde?
Wittig Reaction Provide a mechanism for the formation of CO2 from bis(2-carbopentyloxy-3,5,6-trichlorophenyl)oxalate.
Wittig Reaction Provide a mechanism for the formation of CO2 from bis(2-carbopentyloxy-3,5,6-trichlorophenyl)oxalate.
Wittig Reaction:  synthesis an alkene ( olefin) from the reaction of an aldehyde or a ketone with...
Wittig Reaction:  synthesis an alkene ( olefin) from the reaction of an aldehyde or a ketone with a phosphorous ylide ( phosphorane ). The ylide is produced from phoshonium salt with a base ( NaOH ). The alkene synthesized is trans-9-(2-phenylethenyl)anthracene. 1.) The final product is an E isomer, although a Z isomer could potentially be formed. What is the definition of E and/or Z isomer of alkenes? How the group priority is established? 2.) Speculate why the E isomer is...
A Wittig reaction was performed with the following: 35.22 g methyltriphenylphosphonium bromide, 13.4 g sodium t-pentoxide,...
A Wittig reaction was performed with the following: 35.22 g methyltriphenylphosphonium bromide, 13.4 g sodium t-pentoxide, 51 mL bmimBF4, 10.7 mL 4-methyl-2-pentanone (“methyl isobutyl ketone”). What is the theoretical yield, in grams, of the product of this reaction? Show your calculations.
In a separation by extraction experiment, how would the outcome be different if you used 3M...
In a separation by extraction experiment, how would the outcome be different if you used 3M HCL first instead of 3 M NaOH? -Reaction 1: benzoic acid & sodium hydroxide -Reaction 2: organic product from reaction 1 with hydrochloric acid -Reaction 3: ethyl-4-aminobenzoate with hydrochloric acid -Reaction 4: organic product from reaction 3 with sodium hydroxide
For the Wittig reaction using 208 mg of benzyltriphenylphosphonium chloride, 95 mg of p-bromo benzaldehyde, and...
For the Wittig reaction using 208 mg of benzyltriphenylphosphonium chloride, 95 mg of p-bromo benzaldehyde, and 425 mg of K3PO4 find.. 1. the limiting reactant and the theoretical yield 2. Draw the formal curved arrow electron pushing mechanism for your witting reaction including intermediates and resonance structures if needed. 3. What are the expected H-NMR chemical shifts for the product(s) and state whether they are expected to be a singlet, doublet, triplet, or multiiplet
These questions are from The Wittig Reaction: Chemiluminescence. 1. Predict the order of elution of a...
These questions are from The Wittig Reaction: Chemiluminescence. 1. Predict the order of elution of a mixture of 9-anthraldehyde and (E)-9-(2-phenylethenyl)-anthracene on a TLC plate using a 5:1 hexanes/ethyl acetate eluent mixture. 2. How do you predict that cooling and warming your chemiluminescence reaction mixture after initial mixing will affect the reaction? 3. A glow stick contains: a dye molecule, an oxalate ester, and hydrogen peroxide. Two of these components have to be separated until it is time to use...