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Concept explainers
(a)
Interpretation:
The product should be identified.
Concept introduction:
The pinacol–pinacolone rearrangement:
Pinacol–pinacolone rearrangement is a conversion of 1,2-
(b)
Interpretation:
The reason should be explained for the only one product in the given reaction.
Concept introduction:
The pinacol–pinacolone rearrangement:
Pinacol–pinacolone rearrangement is a conversion of 1,2-diol to a carbonyl compound in the presence of acid via 1,2- shift is called rearrangement is called Pinacol–pinacolone rearrangement.
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Chapter 11 Solutions
Organic Chemistry; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card; Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition)
- The reaction of a nitrile with an alcohol in the presence of a strong acid forms an N-substituted amide. This reaction, known as the Ritter reaction, doesnot work with primary alcohols. a. Why does the Ritter reaction not work with primary alcohols? b. Provide an explanation for why an amide is less susceptible to nucleophilic attack than its corresponding ester.arrow_forwardPlease explain the chosen letter. When benzyl alcohol is oxidized with KMNO4, the product obtained is which of the following compound? a. Benzaldehyde b. Benzoic acid c. CO2 and H2O d. Benzophenonearrow_forwardWhat test will allow you to distinguish between: a. benzyl alcohol and cyclohexanolb. benzyl alcohol and phenol c. cyclohexanol and 1-methylcyclohexanol d. o-cresol and anisolee. benzyl alcohol and anisolearrow_forward
- 5. Draw the structure of following compounds: a. methyl butanoate b. propyl ethanoate c. ethyl propanoate d. ethyl 3-methylhexanoate e. butyl hexanoate f. methyl 2-hexyl-3-oxocyclopentanecarboxylatearrow_forwardDraw the products formed when p-methylaniline (p-CH3C6H4NH2) is treated with each reagent. a. HCl b. CH3COCl c. (CH3CO)2O d. excess CH3I e. (CH3)2C = O f. CH3COCl, AlCl3 g. CH3CO2H h. NaNO2, HCl i. Part (b), then CH3COCl, AlCl j. CH3CHO, NaBH3CNarrow_forwardPhosgene (COCl2) was used as a poison gas in World War I. What product would be formed from the reaction of phosgene with each of the following reagents? a. one equivalent of methanol b. excess methanol c. excess propylamine d. excess waterarrow_forward
- Compare aldehydes and ketones as to (Use acetaldehyde and acetone as examples). 1. Reaction with Tollen’s reagent 2. Reaction with Fehling’s reagent 3. Reaction with dilute NaOHarrow_forward4. WHAT ARE IMINES? HOW ARE THEY FORMED? 5. WHAT IS GRIGNARD REACTION? WHAT CONSTITUTES A GRIGNARD REAGENT? 6. WHAT IS KETO-ENOL TAUTOMERIZATION?arrow_forwardAmino acids such as glycine are the building blocks of large molecules called proteins that give structure to muscle, tendon, hair, and nails. a. Explain why glycine does not actually exist in the form with all atoms uncharged, but actually exists as a salt called a zwitterion. b. What product is formed when glycine is treated with concentrated HCl? c. What product is formed when glycine is treated with NaOH?arrow_forward
- 6. What starting materials are needed to synthesize each compound using the indicated reagent or functional group? a. Synthesize: OH from an ester b. Synthesize: using an organocuprate reagent c. Synthesize: OH using a Grignard reagentarrow_forward6. What starting materials are needed to synthesize each compound using the indicated reagent or functional group? a. Synthesize: OH from an ester b. Synthesize: using an organocuprate reagent 04 using a Grignard reagent c. Synthesize: OHarrow_forwardDraw the product formed when pentanal (CH3 CH₂ CH₂ CH₂ CHO) is treated with each reagent. With some reagents, no reaction occurs. a. NaBH4, CH3OH b. [1] LiAiH4: [2] H₂O c. H₂, Pd-C d. PCC e. Na₂Cr₂O7, H₂SO4, H₂O f. Ag₂O, NH4OH g. [1] CH3 MgBr; [2] H₂O h. [1] C6H5 Li: [2] H₂O i. [1] (CH3)2 CuLi; [2] H₂O J. [1] HC=CNa; [2] H₂O k. [1] CH 3 C=CLI; [2] H₂O 1. The product in (a), then TBDMS-CI, imidazolearrow_forward
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