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.
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Chapter 9 Solutions
EP ORGANIC CHEMISTRY-OWL V2 ACCESS
- 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_forwardDescribe a sequence of reactions by which 3-methyl-1-butyne can be straightforwardly prepared from acetylene.arrow_forwardGive a mechanism that accounts for the organic products of this reaction. Your mechanism must include a transition state that accounts for the stereochemistry of the product and/or reactant. Redraw the reagents as needed. CI OH NaOH, DMSO + NaClarrow_forward
- Ph3P-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_forwardDiphenylacetylene can be synthesized by the double dehydrohalogenation of 1,2-dibromo-1,2-diphenylethene. The sequence starting from (E)-1,2-diphenylethene consists of bromination to give the dibromide, followed by dehydrohalogenation to give a vinylic bromide, then a second dehydrohalogenation to give diphenylacetylene.(a) What is the structure, including stereochemistry, of the vinylic bromide?(b) If the sequence starts with (Z)-1,2-dibromo-1,2-diphenylethene, what is (are) the structure(s) of the intermediate dibromide(s)? What is the structure of the vinylic bromide?arrow_forwardStarting from acetylene and alkyl halides not longer than 4 carbon atoms, show the synthesis of 3-octanol and a ketone. Indicate the reagents in each step.arrow_forward
- Show how to synthesize alkynes by eliminations from alkyl halides and by the additions and substitu- tions of acetylide ions.arrow_forwardProvide the structure of the two organic product(s) which results when 2-bromo-2-methylbutane is treated with sodium ethoxide.arrow_forwardDescribe a sequence of reactions by which meso-2,3-dibromobutane can be prepared from propyne.arrow_forward
- Write a mechanism that accounts for the formation of ethyl isopropyl ether as one of the products in the following reaction. CI OEt HCI EtOH Write the mechanism for step one of this reaction. Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. Write the mechanism for step two of this reaction (where the product of step one reacts with the solvent, ethanol). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. Write the mechanism for the last step of this reaction (formation of ethyl isopropyl ether). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. CI will act as the base in this reaction.arrow_forwardWrite four examples of the condensation reactions of carbonyl compounds, starting with benzaldehyde (C6H5CHO), with appropriate reagents and appropriate reactions. Write down the mechanism of one you want in detail.arrow_forwardGive the product of the following transformation:arrow_forward
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