Interpretation:
The mechanism of given nucleophilic substitution has to be suggested and stereochemistry of product has to be given.
Concept Introduction:
The
The first step of
Frist step is the slow step also rate determining step so the rate of the reaction is depends on the concentration of substrate only.
Nucleophile attacks the both front and back side of carbocation in
Order of the substrate that favored in
In E1 reaction, removal of halide ion forms a stable carbocation and this carbocation is stabilized by formation of double bond by removal of hydrogen.
Trending nowThis is a popular solution!
Chapter 9 Solutions
Organic Chemistry
- Propose a mechanism to account for the formation of 3, 5-dimethyl- pyrazole from hydrazine and 2, 4-pentanedione. Look carefully to see what has happened to each carbonyl carbon in going from starting material to product.arrow_forwardCH3 Ph3P-CHCH3 H3C H3C Aldehydes and ketones are converted into alkenes by means of a direct nucleophilic addition called the Wittig reaction. In the reaction, a triphenylphosphorine ylide, also called a phosphorane, adds to an aldehyde/ketone to give a four-membered cyclic intermediate called an oxaphosphetane. The oxaphosphetane is not isolated but instead spontaneously decomposes to release triphenylphosphine oxide and an alkene. Ph3P-CHCH3 H3C The ylide is formed by reaction of triphenylphosphine, a good nucleophile, with a primary alkyl halide in an S 2 reaction, followed by deprotonation of the carbon with a strong base, such as butyllithium. The carbonyl carbon and the carbon originally bonded to the halogen become the two carbons with the double bond in the product alkene :0: CH3 Com The real value of the Wittig reaction lies in its ability to yield an alkene of predictable structure, as the C-C bond is precisely where the C=O bond was in the reactant and no isomers (other than…arrow_forwardPropose a mechanism to account for the formation of this product.arrow_forward
- What is the product of the reaction and show a possible mechanism for the formation of the product?arrow_forwardProvide mechanisms for this reactionarrow_forwardThe product formed as a result of the reaction between cyclohexanone and 3-butene-2-one write down the product and mechanism of the reaction.arrow_forward
- Complete these reactions, showing the stereochemistry of the productarrow_forwardPh3P-CHCH3 H₂C H3C Aldehydes and ketones are converted into alkenes by means of a direct nucleophilic addition called the Wittig reaction. In the reaction, a triphenylphosphorine ylide, also called a phosphorane, adds to an aldehyde/ketone to give a four-membered cyclic intermediate called an oxaphosphetane. The oxaphosphetane is not isolated but instead spontaneously decomposes to release triphenylphosphine oxide and an alkene. CH3 00 + The ylide is formed by reaction of triphenylphosphine, a good nucleophile, with a primary alkyl halide in an SN2 reaction, followed by deprotonation of the carbon with a strong base, such as butyllithium. The carbonyl carbon and the carbon originally bonded to the halogen become the two carbons with the double bond in the product alkene X m CH3 The real value of the Wittig reaction lies in its ability to yield an alkene of predictable structure, as the C=C bond is precisely where the C=O bond was in the reactant and no isomers (other than E/Z isomers)…arrow_forwardProvide a series of synthetic steps by which p-nitrophenol can be prepared from benzene.arrow_forward