Concept explainers
(a)
Interpretation:
The mechanism for transformation of compound 2 to 3 must be drawn and the leaving group must be identified.
Concept Introduction :
Grignard reagents are one class of
(b)
Interpretation:
The irreversible nature of the conversion from 2 to 3 must be explained.
Concept Introduction :
The irreversible reactions are those in which starting materials are not obtained easily from the product.
(c)
Interpretation:
Conversion of 3 to 4 in aqueous acid must be shown with SN1 and SN2 mechanism.
Concept Introduction :
Ether hydrolysis can follow both SN1 and SN2 pathway depending on the structure of the substrate.
(d)
Interpretation:
The by-product alcohol must be identified which is formed during the conversion of 3 to 4.
Concept Introduction :
The ether cleavage produces two alcohols corresponding to the two substituents of the ether.
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- H3C. 00 H3C. CH3 XII HO: OCH3 Aldehydes and ketones react reversibly with two equivalents of alcohol in the presence of an acid catalyst to give acetals. Alcohols are poor nucleophiles, and so protonation of the carbonyl oxygen is used to make the carbonyl carbon a stronger electrophile. Addition of the first equivalent of alcohol gives a hemiacetal, a hydroxyether. Addition of the second equivalent of alcohol is accompanied by loss of water to yield the product acetal. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions 2 CH₂OH HCI catalyst CH3 H3C H-OH₂ H3CO OCH3 CH3 H3C. H₂O: OCH3 CH3 H₂O Чаarrow_forward3. The following reaction is used in the industrial synthesis of the antiviral drug, oseltamivir (Tamiflu), by the pharmaceutical company, Roche. Propose a mechanism for this transformation. OEt Hint: first, the acetal is hydrolyzed using water and triflic acid (a very strong acid), then the resulting diol can form an acetal with pentan-3-one. NH,-H3PO, oseltamivir OEt OEt TFOH H20 OMs OMs TFOH = F3C-S-OH triflic acidarrow_forward4. Determine the appropriate reagents to achieve the following transformations. 요 Η Ph Ph Ηarrow_forward
- Carboxylic acids can also act as a nucleophile in substitution reactions (your textbook shows this!). What is the major expected product of the following reaction? ola పహద్డనిు Но CH3 Br CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 A в Darrow_forwardWilliamson Ether Synthesis of Phenacetin Background: Synthesize phenacetin from acetaminophen (Tylenol) via a Williamson ether synthesis.The Williamson ether synthesis is one of the simplest methods used to make ethers. The reaction is named after Alexander Williamson, who discovered the reaction in 1850. In this reaction, an alkoxide anion reacts with an alkyl halide via a substitution reaction. RO-Na+ + R` – X → R-O-R` + NaX Alkoxides are strong nucleophiles that tend to react via an SN2 mechanism. As a result, the reaction works best with primary alkyl halides. In a traditional Williamson ether synthesis, the alkoxide is generated by reacting sodium hydride (NaH) with an alcohol. ROH + NaH → RO-Na+ + H2 While this reaction is very efficient, it does pose a fire hazard, as it is possible for hydrogen gas to ignite. In this lab, the alkoxide will be created using sodium hydroxide (NaOH). This is a much safer option, eliminating a…arrow_forwardShow how the product formed as a result of the reaction can be synthesized using the starting materials given below. Any reagent needed can be used and you may need more than one step. c) HO, al OH d) b) Онarrow_forward
- Propose a synthesis of the compound shown below starting with cyclohexenone and any other carbon compounds of four carbons or less. o cyclohexenone Propose OscerSyn Synthesis 4arrow_forwardComplete the following transformations by providing reagents or products: Ph 1) KMnO4, NaOH H₂O, heat 2) H₂O, H₂O+ CH3 39 CH3arrow_forward1. Propose reasonable mechanisms for the following transformations: OH H+ to H*arrow_forward
- 13). What is the major product of the following two reactions? H₂ H3C H3C NH (A) H3C ОН H3C NH₂ OH-, then H2O (D) H3C H₂ (В) CH3 ? H3C H3C (E) ОН NH (C) CH3 -CH₂arrow_forward4. What organometallic and carbonyl compound could be used to prepare the following compound? Propose two different carbonyl starting materials and corresponding organometallic reagents. OH OCH 3arrow_forward2. What organometallic and carbonyl compound could be used to prepare the following compounds? Propose two different carbonyl starting materials and corresponding organometallic reagents for each compound. HO OHarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning