Interpretation:
The stereochemical formula for A, B, C, and D is to be proposed and the reactions involved in these transformation are to be outline.
Concept introduction:
Electrophiles are electron-deficient species, which has positive or partially positive charge. Lewis acids are electrophiles, which accept electron pair.
Nucleophiles are electron-rich species, which has negative or partially negative charge. Lewis bases are nucleophiles, which donate electron pair.
Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction.
Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.
Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.
Reduction is a process in which hydrogen atoms are added to a compound.
The molecules which are non-superimposable or not identical with their mirror images are known as chiral molecules.
The stereoisomers which are non-superimposable on each other and not mirror images of each other are known as diastereomers.
The achiral compounds in which plane of symmetry is present internally and consists of chiral centres are known as meso compounds, but they are optically inactive.
Enantiomers are stereoisomers whose molecules contain nonsuperimposable mirror images.
A chiral molecule is one that has a nonsuperimposable mirror image and an achiral molecule is one that has a superimposable mirror image.
The compounds having the same molecular formula and connectivity, but different spatial arrangement are known as stereo-isomers.
A compound that rotates the plane-polarized light in clockwise direction is called dextrorotary.
A compound that rotates the plane-polarized light in anti-clockwise direction is called levorotary.
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ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
- Amines are converted into alkenes by a two-step process called Hofmann elimination. SN2 reaction of the amine with an excess of CH3I in the first step yields an intermediate that undergoes E2 reaction when treated with silver oxide as base. Pentylamine, for example, yields 1-pentene. Propose a structure for the intermediate, and explain why it readily undergoes elimination.arrow_forwardNonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forwardKetones and aldehydes react with sodium acetylide (the sodium salt of acetylene) to give alcohols, as shown in the following example: R₁ OH 1. HC=C: Na* + R₂ Rí R2 2. H3O+ HC Draw the structure of the major reaction product when the following compound reacts with sodium acetylide, assuming that the reaction takes preferentially from the Re face of the carbonyl group. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • You do not have to explicitly draw H atoms. •If a group is achiral, do not use wedged or hashed bonds on it. E CH3 H3Carrow_forward
- Treatment of cis-4-bromocyclohexanol with HO– affords compound A and cyclohex-3-en-1-ol. Treatment of trans-4- bromocyclohexanol under the same conditions forms compound B and cyclohex-3-en-1-ol. A and B contain different functional groups and are not isomers of each other. Propose structures for A and B and offer an explanation for their formation.arrow_forwardH3C N- H₂NNH₂ H⭑ CH3 H3C IN CH3 Hydrazine reacts with 2,4-pentanedione to yield 3,5-dimethylpyrazole. Including protonations and deprotonations, the reaction takes 12 steps. Write out the mechanism on a sheet of paper and then draw the structure of the product of step 6. • You do not have to consider stereochemistry. •You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • In an elimination step, include the structure of the leaving group, but draw it in its own sketcher. Separate structures with + signs from the drop-down menu. ? Sn th Previous Nextarrow_forwardTreatment of anthranilic acid with nitrous acid gives an intermediate, A, that contains a diazonium ion and a carboxylate group. When this intermediate is heated in the pres- ence of furan, a tricyclic compound is formed. Propose a structural formula for com- pound A and a mechanism for the formation of the tricyclic product. COOH NANO, HCI + CO, + N2 NH2 Anthranilic acidarrow_forward
- H8.arrow_forwardSharpless epoxidation of allylic alcohol X forms compound Y. Treatment of Y with NaOH and C6H5SH in an alcohol–water mixture forms Z. Identify the structure of Y and draw a mechanism for the conversion of Y to Z . Account for the stereochemistry of the stereogenic centers in Z. Z has been used as an intermediate in the synthesis of chiral carbohydrates.arrow_forwardGive two sets of reactants (each set including an alkyl halide and a nucleophile) that could be used to synthesize the following ether:arrow_forward
- When 3-methyl-1-butene reacts with HBr, two alkyl halides are formed: 2-bromo-3-methylbutane and 2-bromo-2-methylbutane. Propose a mechanism that explains the formation of these two products.arrow_forwardA synthetic organic molecule, G, which contains both aldehyde and ether functional groups, is subjected to a series of reactions in a multi-step synthesis pathway. In the first step, G undergoes a Wittig reaction, leading to the formation of an alkene, H. Subsequently, H is treated with an ozone (O3) reagent followed by a reducing agent in an ozonolysis reaction, resulting in the formation of two different products, I and J. Considering the functional groups present in G and the nature of the reactions involved, what are the most probable structures or functional groups present in products I and J? A. I contains a carboxylic acid group, and J contains an aldehyde group. B. I contains a ketone group, and J contains an alcohol group. C. I and J both contain aldehyde groups. D. I contains an ester group, and J contains a ketone group. Don't use chat gpt.arrow_forwardCompound A is an optically active alcohol. Treatment with chromic acid converts A into a ketone, B. In a separate reaction, A is treated with PB13, converting A into compound C. Compound C is purified, and then it is allowed to react with magnesium in ether to give a Grignard reagent, D. Compound B is added to the resulting solution of the Grignard reagent. After hydrolysis of the initial product (E), this solution is found to contain 3,4-dimethylhexan-3-ol. Propose structures for compounds A, B, C, D, and E. Click here to have access to www.autodraw.com/arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning