Interpretation:
The product in each of the given reactions from their
Concept Introduction:
In the
The chemical shift of a particular proton in the compound depends on the environment of the proton.
The signal of a particular proton is split by the presence of protons in vicinal position.
Index of hydrogen deficiency is calculated as
Presence of electronegative atoms in the structure de-shields the signals from their normal values.
The ideal range for protons in
Epoxide rings are readily opened with cleavage of the carbon-oxygen bond when attacked by nucleophiles. Grignard reagents and organ lithium reagents react with epoxides by serving a source of nucleophilic carbon.
The nucleophilic carbon atom in the organometallic reagent attacks on the less substituted (less sterically hindered) carbon atom in the epoxide.
The mechanism resembles and
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ORGANIC CHEMISTRY (LL)-W/SOLN.>CUSTOM<
- Provide the complete mechanism using curved arrow formalism for the reaction of p-chlorobenzonitrile in aqueous acid. State which layer (aqueous or organic) the product(s) are isolated in. Give the number of peaks observed in the 13C NMR spectra for the product formed.arrow_forwardIdentify products A and B from the given 1H NMR data. Treatment of acetone [(CH3)2C=O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1H) ppm. What is the structure of B?arrow_forwardReaction of unknown A with HCl forms chlorohydrin B as the major product. A shows no absorptions in its IR spectrum at 1700 cm−1 or 3600–3200 cm−1, and gives the following 1H NMR data: 1.4 (doublet, 3 H), 3.0 (quartet of doublets, 1 H), 3.5 (doublet, 1 H), 3.8 (singlet, 3 H), 6.9 (doublet, 2 H), and 7.2 (doublet, 2 H) ppm. (a) Propose a structure for A, including stereochemistry. (b) Explain why B is the major product in this reaction.arrow_forward
- Illustrate 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_forwardReaction between this aldehyde and ketone in base gives a compound A with the proton NMR spectrum: ô 1.10 (9H, s), 1.17 (9H, s), 6.4 (1H, d, J 15), and 7.0 (1H, d, J 15). What is its structure? (Don't forget stereochemistry!). When this compound reacts with HBr it gives compound B with this NMR spectrum: õu 1.08 (9H, s), 1.13 (9H, s), 2.71 (1H, dd, J 1.9, 17.7), 3.25 (dd, J10.0, 17.7), and 4.38 (1H, dd, J 1.9, 10.0). Suggest a structure, assign the spectrum, and give a mechanism for the formation of B. H base C11H₂00 HBr B C11H₂1 Broarrow_forwardReaction of (CH3)3CCHO with (C6H5)3P=C(CH3)OCH3, followed by treatment with aqueous acid, affords R (C7H14O). R has a strong absorption in its IR spectrum at 1717 cm−1 and three singlets in its 1H NMR spectrum at 1.02 (9 H), 2.13 (3 H), and 2.33 (2 H) ppm. What is the structure of R? We will learn about this reaction in Chapter 18.arrow_forward
- Reaction of p-cresol with two equivalents of 2-methylprop-1-ene affords BHT, a preservative with molecular formula C15H24O. BHT gives the following 1H NMR spectral data: 1.4 (singlet, 18 H), 2.27 (singlet, 3 H), 5.0 (singlet, 1 H), and 7.0 (singlet, 2 H) ppm. What is the structure of BHT? Draw a stepwise mechanism illustrating how it is formed.arrow_forwardProvide the correct product for the following series of transformations. Hint: The product has a 1H NMR spectrum with only 2 resonances with relative H integrations of 3:1.arrow_forwardProvide the complete mechanism using curved arrow formalism for the reaction of p-isopropxlbenzoic acid undergoing nitration. Tell how many peaks in the 'H and 13C NMR spectrum that would be observed for the final product.arrow_forward
- Identify the following compound from its IR and proton NMR spectra. C,H1,0: 'H NMR 8 3.31 (3H, s); 8 2.41 (1H, s); & 1.43 (6H, s) IR: 2110, 3300 cm- (sharp)arrow_forwardDraw all resonance structures of the conjugate bases formed by removalof the labeled protons (Ha, Hb, and Hc) in cyclohexane-1,3-dione andacetanilide. For each compound, rank these protons in order ofincreasing acidity and explain the order you chose.arrow_forwardReaction of (CH3)3CCHO with (C6H5)3P=C(CH3)OCH3, followed bytreatment with aqueous acid, affords R (C7H14O). R has a strong absorption in its IR spectrum at 1717 cm−1 and three singlets in its 1H NMR spectrum at 1.02 (9 H), 2.13 (3 H), and 2.33 (2 H) ppm. What is thestructure of R?arrow_forward
- EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT