Concept explainers
(a)
Interpretation: The product formed by the treatment of
Concept introduction: Monosaccharides are the small units of simple sugars. The hydroxyl groups of monosaccharides are converted into the ether groups in presence of base and
Answer to Problem 28.49P
The product formed by the treatment of
Figure 1
Explanation of Solution
The conversion of hydroxyl groups of
Figure 2
The product formed by the treatment of
(b)
Interpretation: The product formed by the treatment of
Concept introduction: Monosaccharides are the small units of simple sugars The hydroxyl groups of monosaccharides are converted into the ether groups in presence of base and alkyl halide.
Answer to Problem 28.49P
The products formed by the treatment of
Figure 3
Explanation of Solution
The two anomers are formed by the treatment of monosaccharides with methanol in the presence of hydrochloric acid. One product with methoxy group on the equatorial position and other product with methoxy group on the axial position. The corresponding chemical reaction is shown below.
Figure 4
The products formed by the treatment of
(c)
Interpretation: The product formed by the treatment of
Concept introduction: Monosaccharides are the small units of simple sugars. The hydroxyl groups of monosaccharides are converted into the ether groups in presence of base and alkyl halide.
Answer to Problem 28.49P
The product formed by the treatment of
Figure 5
Explanation of Solution
In the presence of acetic anhydride and pyridine, the conversion of alcoholic groups in
Figure 6
The product formed by the treatment of
(d)
Interpretation: The product formed by the treatment of
Concept introduction: Monosaccharides are the small units of simple sugars. The hydroxyl groups of monosaccharides are converted into the ether groups in presence of base and alkyl halide.
Answer to Problem 28.49P
The products formed by the treatment of
Figure 7
Explanation of Solution
The first step is the conversion of hydroxyl groups of gulose into the ether groups in presence of base and methyl iodide as shown in Figure 2.
The product
Figure 8
The products formed by the treatment of
(e)
Interpretation: The product formed by the treatment of
Concept introduction: Monosaccharides are the small units of simple sugars The hydroxyl groups of monosaccharides are converted into the ester groups in presence of base and acetic anhydride or acetyl chloride.
Answer to Problem 28.49P
The products formed by the treatment of
Figure 9
Explanation of Solution
The conversion of alcoholic groups of product
Figure 10
The products formed by the treatment of
(f)
Interpretation: The product formed by the treatment of
Concept introduction: Monosaccharides are the small units of simple sugars. The hydroxyl groups of monosaccharides are converted into the ether groups in presence of base and alkyl halide.
Answer to Problem 28.49P
The products formed by the treatment of
Figure 11
Explanation of Solution
The conversion of hydroxyl groups of product
Figure 12
The products formed by the treatment of
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Chapter 28 Solutions
Organic Chemistry
- Draw the product formed when (CH3)2CHOH is treated with each reagent. a.SOCl2, pyridine b. TsCl, pyridine c.H2SO4 d.HBr e.PBr3, then NaCN f.POCl3, pyridinearrow_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_forwardDraw the products formed when a-D-gulose is treated with each reagent. a. CH3I, Ag,0 b. CH,OH, HCI c. CeHsCH2CI, Ag20 d. CgHsCH2OH, HCI e. Ac20, pyridine f. CeHsCOCI, pyridine g. The product in (a), then H3O* h. The product in (b), then Ac,0, pyridine i. The product in (g), then CeHsCH2CI, Ag20 j. The product in (d), then CH3I, Ag20 но OH но OH OH D-gulosearrow_forward
- Draw the products formed when each compound is treated with CH;CH,COCI, AICI3. CH(CH3)2 N(CH)2 Br CH3 CH(CH)2 a. b. C. d. е.arrow_forwardDraw the products of each reaction. CH3 a. CH3-C-CH,CH3 HCI HI OH HBr b. C. OHarrow_forwardDraw the products formed when CH3CH2CH2CH2OTs is treated with each reagent.a. CH3SHb. NaOCH2CH3c. NaOHd. KOC(CH3)3arrow_forward
- Determine the products of each carboxylic acid reaction. a. CH3-CH2-CH2-CH,-C-OH + H,SO, CH, — CH,— он HO. b. CH2 heat CH2 C-OH CH2arrow_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_forwardDraw the organic product(s) formed when CH3CH2CH2OH is treated with each reagent. a.H2SO4 b.NaH c.HCl + ZnCl2 d.HBr e.SOCl2, pyridine f.PBr3 g.TsCl, pyridine h. [1] NaH; [2] CH3CH2Br [1] i.TsCl, pyridine; [2] NaSH j.POCl3, pyridinearrow_forward
- Draw the products of combustion of each alkane. a. CH;CH,CH,CH2CH(CH3)2 b.arrow_forwardWhat product is formed when D-Gulose is treated with a. CH3I, Ag2O b. The product in (a), then H3O+ c. The product in (b), then C6H5CH2Cl, Ag2Oarrow_forwardMaltose is a carbohydrate present in malt, the liquid obtained from barley and other grains. Although maltose has numerous functional groups, its reactions are explained by the same principles we have already encountered.a. Label the acetal and hemiacetal carbons.b. What products are formed when maltose is treated with each of these reagents: [1] H3O+; [2] CH3OH and HCl; [3] excess NaH, then excess CH3I?c. Draw the products formed when the compound formed in Reaction [3] of part (b) is treated with aqueous acid.The reactions in parts (b) and (c) are used to determine structural features of carbohydrates like maltose.arrow_forward
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