Detailed mechanism for the given reaction of an α,β- unsaturated ketone with a conjugated Wittig reagent to produce a relatively highly strained bicyclic compound is to be drawn. Concept introduction: The Wittig reaction is one of the primary methods of preparation of alkene from aldehyde or ketone using a reagent called ylide. The ylide is a neutral molecule having positively charged phosphorous atom bonded to negatively charged carbon atom. The negatively charged carbon of an ylide acts as a nucleophile and attacks the electrophilic carbon of carbonyl group and forms betaine, which has the negative charge on the oxygen and positive charge on the phosphorus atom. The reaction proceeds with the formation of four membered ring intermediate called an oxaphosphetane by forming a bond between the negatively charged oxygen and positively charged phosphorus. In case of α,β- unsaturated ketone, the negatively charged carbon attacks the β carbon instead of the carbonyl carbon and forms the bicyclic compound.

Question

Want to see the full answer?

Answer 1

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 17, Problem 17.70P

Interpretation Introduction

Interpretation:

Detailed mechanism for the given reaction of an α,β- unsaturated ketone with a conjugated Wittig reagent to produce a relatively highly strained bicyclic compound is to be drawn.

Concept introduction:

The Wittig reaction is one of the primary methods of preparation of alkene from aldehyde or ketone using a reagent called ylide. The ylide is a neutral molecule having positively charged phosphorous atom bonded to negatively charged carbon atom. The negatively charged carbon of an ylide acts as a nucleophile and attacks the electrophilic carbon of carbonyl group and forms betaine, which has the negative charge on the oxygen and positive charge on the phosphorus atom. The reaction proceeds with the formation of four membered ring intermediate called an oxaphosphetane by forming a bond between the negatively charged oxygen and positively charged phosphorus.

In case of α,β- unsaturated ketone, the negatively charged carbon attacks the β carbon instead of the carbonyl carbon and forms the bicyclic compound.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

1) Suppose 0.1 kg ice at 0°C (273K) is in 0.5kg water at 20°C (293K). What is the change in entropy of the ice as it melts at 0°? To produce the original "water gas" mixture, carbon (in a combustible form known as coke) is reacted with steam: 131.4 kJ + H20(g) + C(s) → CO(g) + H2(g) From this information and the equations in the previous problem, calculate the enthalpy for the combustion or carbon to form carbon dioxide. kindly show me how to solve both parts of the same long problem. Thanks

we were assigned to dilute 900ppm in to 18ppm by using only 250ml vol flask. firstly we did calc and convert 900ppm to 0.9 ppm to dilute in 1 liter. to begin the experiment we took 0,225g of kmno4 and dissolved in to 250 vol flask. then further we took 10 ml sample sol and dissolved in to 100 ml vol flask and put it in to a spectrometer and got value of 0.145A . upon further calc we got v2 as 50ml . need to find DF, % error (expval and accptVal), molarity, molality. please write the whole report. thank you The format, tables, introduction, procedure and observation, result, calculations, discussion and conclusion

Q5. Predict the organic product(s) for the following transformations. If no reaction will take place (or the reaction is not synthetically useful), write "N.R.". Determine what type of transition state is present for each reaction (think Hammond Postulate). I Br₂ CH3 F2, light CH3 Heat CH3 F₂ Heat Br2, light 12, light CH3 Cl2, light No

Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 17, Problem 17.70P

Interpretation Introduction

Interpretation:

Detailed mechanism for the given reaction of an α,β- unsaturated ketone with a conjugated Wittig reagent to produce a relatively highly strained bicyclic compound is to be drawn.

Concept introduction:

The Wittig reaction is one of the primary methods of preparation of alkene from aldehyde or ketone using a reagent called ylide. The ylide is a neutral molecule having positively charged phosphorous atom bonded to negatively charged carbon atom. The negatively charged carbon of an ylide acts as a nucleophile and attacks the electrophilic carbon of carbonyl group and forms betaine, which has the negative charge on the oxygen and positive charge on the phosphorus atom. The reaction proceeds with the formation of four membered ring intermediate called an oxaphosphetane by forming a bond between the negatively charged oxygen and positively charged phosphorus.

In case of α,β- unsaturated ketone, the negatively charged carbon attacks the β carbon instead of the carbonyl carbon and forms the bicyclic compound.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 17, Problem 17.70P

Interpretation Introduction

Interpretation:

Detailed mechanism for the given reaction of an α,β- unsaturated ketone with a conjugated Wittig reagent to produce a relatively highly strained bicyclic compound is to be drawn.

Concept introduction:

The Wittig reaction is one of the primary methods of preparation of alkene from aldehyde or ketone using a reagent called ylide. The ylide is a neutral molecule having positively charged phosphorous atom bonded to negatively charged carbon atom. The negatively charged carbon of an ylide acts as a nucleophile and attacks the electrophilic carbon of carbonyl group and forms betaine, which has the negative charge on the oxygen and positive charge on the phosphorus atom. The reaction proceeds with the formation of four membered ring intermediate called an oxaphosphetane by forming a bond between the negatively charged oxygen and positively charged phosphorus.

In case of α,β- unsaturated ketone, the negatively charged carbon attacks the β carbon instead of the carbonyl carbon and forms the bicyclic compound.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 17, Problem 17.70P

Interpretation Introduction