Concept explainers
Interpretation:
The preparation of
Concept introduction:
The carboxylic acids contain carboxylic
Aldehydes and ketones contain carbonyl
Lithium aluminum hydride and sodium borohydride are strong reducing agents. They are inorganic compounds which are used as the reducing agents in organic synthesis. They are used for the conversion of carboxylic acids, aldehydes and ketones into primary and secondary alcohols.
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ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
- only need d-farrow_forward19.57 Because phenol (C6H5OH) is less acidic than a carboxylic acid, it can be deprotonated by NaOH but not by the weaker base NaHCO3. Using this information, write out an extraction sequence that can be used to separate C6H5OH, benzoic acid, and cyclohexanol. Show what compound is present in each layer at each stage of the process, and if it is present in its neutral or ionic form.arrow_forward• PRACTICE PROBLEM 18.14 Show how you could employ enamines in syntheses of the following compounds: Een önös (c) (a) (b) (d) OEtarrow_forward
- Rank the compounds in each of the following groups in order of their reactivity to electrophilic substitution: (a) Nitrobenzene, phenol, toluene, benzene (b) Phenol, benzene, chlorobenzene, benzoic acid (c) Benzene, bromobenzene, benzaldehyde, anilinearrow_forwardOctinoxate is an unsaturated ester used as an active ingredient in sunscreens. (a) What carbonyl compounds are needed to synthesize this compound using a condensation reaction? (b) Devise a synthesis of octinoxate from the given organic starting materials and any other needed reagents.arrow_forward19.54 Predict the major product(s) from the treatment of acetone with the following: (d) [H], (CH3)2NH, (-H2O) (e) [H], NH2NH2, (-H2O) (f) [H], NH2OH, (-H2O) (g) NaBH4, MeOH (h) RCO3H (i) HCN, KCN (j) EtMgBr followed by H₂O (k) (C6H5)3P=CHCH2CH3 (1) LIAIH, followed by H2Oarrow_forward
- Ibufenac, a para-disubstituted arene with the structureHO2CCH2C6H4CH2CH(CH3)2 , is a much more potent analgesic thanaspirin, but it was never sold commercially because it caused livertoxicity in some clinical trials. Devise a synthesis of ibufenac frombenzene and organic halides having fewer than five carbons.arrow_forwardDraw a structural formula for the product formed by treating butanal with each reagent. (a) LiA1H4LiA1H4 followed by H2OH2O (b) NaBH4NaBH4 in CH3OH/H2O (c) H2/Pt (d) Ag(NH3)2+in NH3/H2O (e) H2CrO4, heat (f) HOCH2CH2OH,HClarrow_forward16.51 Propose a plausible mechanism for the following transformation: Heatarrow_forward
- 17.36 Tamoxifen is an estrogen receptor modulator that is used in the treatment of breast cancer. Provide the missing reagents and the structure of compound A in the synthesis of tamoxifen. Page 707 HO (CH3)2N 1. C,H,MgBr 2. H + Compound A (CH3)2N Tamoxifenarrow_forwardGive clear handwritten solarrow_forward18.31 Aldehydes that have no a hydrogen undergo an intermolecular oxidation-reduction called the Cannizzaro reaction when they are treated with concentrated base. An example is the following reaction of benzaldehyde: ororo H HO™ OH H₂O 2 + (a) When the reaction is carried out in D₂O, the benzyl alcohol that is isolated contains no deuterium bound to carbon. It is CBH-CH₂OD. What does this suggest about the mechanism for the reaction? (b) When (CH3)2CHCHO and Ba(OH)₂/H₂O are heated in a sealed tube, the reaction produces only (CH3)₂CHCH₂OH and [(CH3)₂CHCO₂]2Ba. Provide an explanation for the formation of these products.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning