Two configurations can actually be envisioned for the transition state in the DMDO
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- (b) Analyze the major monosubstitution product from the Friedel-Crafts reaction of benzene with 1-chloro-2-methylpropane in the presence of AlCl3. Show your analysis using a mechanistic explanation. (c) Identify the carboxylic acid chloride that might be used in a Friedel-Crafts acylation reaction to prepare each of the following acylbenzene. or (i) Oarrow_forwardCompound C10H16 presents a series of reactions that are shown in the scheme below. Write thestructures of compound A-E. Remember that ozonolysis is the product of an oxidative breakdown of a bonddouble, therefore, consider that in solving this problem your product is a key compound.arrow_forward(a) Write the structures of main products when benzene diazonium chloride reacts with the following reagents :(i) H3PO2 + H2O (ii) CuCN/KCN (iii) H2O(b) Arrange the following in the increasing order of their basic character in an aqueous solution :C2H5NH2, (C2H5)2NH, (C3H5)3N(c) Give a simple chemical test to distinguish between the following pair of compounds :C6H5—NH2 and C6H5—NH—CH3arrow_forward
- 4. (A) A medicinal chemist wished to make a series of aromatic molecules bearing a ketone and thioether group with ortho, meta, or para relationships. To achieve this, they propose using nucleophilic aromatic substitution treating the corresponding ortho, meta, and para aryl chlorides with sodium ethanethiolate (NaSEt). Predict which of these reactions will likely work and which will likely fail. Provide a mechanistic explanation why. SET O NasEt EtS glagol Glal ol heat EtS target molecules EtS (B) Would the analogous reactions using EtMgBr instead of NaSEt be more or less likely to work? Explain why or why not. لمسلم EtMgBrarrow_forwardIllustrate the resonance effect of the methoxy group -OCH3, on the structure of the benzene ring. Draw all the oissuvke resonance forms of methoxybenzene, including the hybrid Based on the structures, explain how the presence of the -OCH3 group affects: (i) the reactivity of the benzene ring towards electrophilic attack (ii) the orientation or point of attack of an incoming electrophilic reagent on the benzene ring.arrow_forwardFor EACH of the following reactions (a)-(d) provide a curved arrow mechanism and where appropriate briefly comment on any issues of selectivity that arise. (a) (b) (c) CHO MeO OMe 3 OH MeO NH OEt Me (i) Ph3P=CBr2 (ii) "BuLi (2 equivs) (iii) Mel + H₂SO4 (cat) OMe H₂O Me3Si * TfO OMe O MeCN CO₂Me MeO CsF, NaHCO3 Me COMe OMearrow_forward
- In depth explanation of each, please.arrow_forward16.55 Working backwards, deduce the starting material that led to the indicated product through the defined reactions. (1) MsCl, pyr (2) KCN, DMF (a) A (1) (a) NaH; (b) HCOCH 3 (2) mCPBA (3) MeMgBr; H3O+ (4) NaH, Mel OMe X (b) B (3) MeMgBr; H₂O+ (4) H₂NNH₂, cat. HA (5) KOH, Aarrow_forward2arrow_forward
- Give explanation of the correct option and explanation of the incorrect options.arrow_forward(a) Given and Scara were given a task of synthesising (2-methylprop-1- enyl)cyclohexane 2 (A potential TB drug). After a brief discussion with each other, Given proposed Method A to synthesise 2 from cyclohexanecarbaldehyde 1 while Scara proposed Method B that started from hydroxymethylcyclohexane 3. When designing a synthetic route for drug molecule, you have to make sure the synthetic process is as efficient as possible (e.g. few synthetic steps, mostly making one product and more). THF A Ph Ph Ph B 3 1. PCC 2. isopropyl magnesium vromide 3. H₂SO4 100 °C OH Method B is not preferred synthetic route due to the number of steps involve (3 steps vs 1 step for Method A). What else is making method A unfavorable synthetic method? Use curly arrows to explain this effect. (Ctrl) -arrow_forward5. Optically pure 2-octyl sulfonate was treated with varying mixtures of water and dioxane, and the optical purity of the resulting product (2-octanol) was found to vary with the ratio of water to dioxane, as shown in the following table (J. Am. Chem. Soc. 1965, 87, 287-291). Given that dioxane possesses fairly nucleophilic oxygen atoms, provide a complete mechanism that explains the variation in in the product's optical purity due to changes in solvent composition. Hint, the solvent is doing more here than just dissolving.. it is partaking in the reaction. Solvent Ratio (water : dioxane) 25:75 50: 50 75: 25 100 :0 Optical purity of (S)-2-octanol 77% 88% 95% 100% H20 он (R)-2-Octyl sulfonate (optically pure) (S)-2-Octanol (dioxane)arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning