Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 28, Problem 28.21P
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Interpretation: The structure of
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Predict the products obtained when d-galactose reacts with each reagent. NaOH, H2O
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Chapter 28 Solutions
Organic Chemistry
Ch. 28 - Prob. 28.1PCh. 28 - Prob. 28.2PCh. 28 - Label each stereogenic center as R or S. a. b. c....Ch. 28 - Convert the ball-and-stick model to a Fischer...Ch. 28 - Prob. 28.5PCh. 28 - Prob. 28.6PCh. 28 - Prob. 28.7PCh. 28 - Prob. 28.8PCh. 28 - Prob. 28.9PCh. 28 - Prob. 28.10P
Ch. 28 - Prob. 28.11PCh. 28 - Prob. 28.12PCh. 28 - Prob. 28.13PCh. 28 - Prob. 28.14PCh. 28 - Prob. 28.15PCh. 28 - Prob. 28.16PCh. 28 - Prob. 28.17PCh. 28 - Draw a stepwise mechanism for the following...Ch. 28 - Prob. 28.19PCh. 28 - Prob. 28.20PCh. 28 - Prob. 28.21PCh. 28 - Prob. 28.22PCh. 28 - Draw the products formed when D-arabinose is...Ch. 28 - Prob. 28.24PCh. 28 - Prob. 28.25PCh. 28 - Prob. 28.26PCh. 28 - Prob. 28.27PCh. 28 - Prob. 28.28PCh. 28 - Prob. 28.29PCh. 28 - Prob. 28.30PCh. 28 - Prob. 28.31PCh. 28 - Prob. 28.32PCh. 28 - Prob. 28.33PCh. 28 - Prob. 28.34PCh. 28 - Problem-28.35
Draw the structures of the...Ch. 28 - Prob. 28.36PCh. 28 - 28.37 Convert each ball-and-stick model to a...Ch. 28 - Prob. 28.38PCh. 28 - Prob. 28.39PCh. 28 - 28.40 Convert each compound to a Fischer...Ch. 28 - Prob. 28.41PCh. 28 - Prob. 28.42PCh. 28 - 28.43 Draw a Haworth projection for each compound...Ch. 28 - Prob. 28.44PCh. 28 - 28.45 Draw both pyranose anomers of each...Ch. 28 - Prob. 28.46PCh. 28 - Prob. 28.47PCh. 28 - Prob. 28.48PCh. 28 - Prob. 28.49PCh. 28 - 28.50 Draw the products formed when D-altrose is...Ch. 28 - Prob. 28.51PCh. 28 - Prob. 28.52PCh. 28 - Prob. 28.53PCh. 28 - Prob. 28.54PCh. 28 - Prob. 28.55PCh. 28 - Prob. 28.56PCh. 28 - Prob. 28.57PCh. 28 - 28.58 Draw a stepwise mechanism for the following...Ch. 28 - Prob. 28.59PCh. 28 - Prob. 28.60PCh. 28 - Prob. 28.61PCh. 28 - Prob. 28.62PCh. 28 - Prob. 28.63PCh. 28 - Prob. 28.64PCh. 28 - Prob. 28.65PCh. 28 - Prob. 28.66PCh. 28 - Prob. 28.67PCh. 28 - Prob. 28.68PCh. 28 - Prob. 28.69PCh. 28 - Prob. 28.70PCh. 28 - 28.71 Draw a stepwise mechanism for the following...
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- The following structure is a ring form of D-lyxose. When D-lyxose is written in its open-chain form: CH₂OH OH OH pl H OH H H Select one: O the hydroxyls on C-2 and C-3 are on the left side while the hydroxyl on C-4 is the right side. O the hydroxyls on C-3 and C-4 are on the right side while the hydroxyl on C-2 is the left side. O the hydroxyls on C-3 and C-4 are on the left side while the hydroxyl on C-2 is the right side. O the hydroxyls on C-2 and C-3 are on the right side while the hydroxyl on C-4 is the left side. Which of the following is NOT a photochemical reaction? Select one: COLCH, CO₂CH3 O O O x (₁ disrotatory A Tas conrotatory 125 + 125arrow_forward5)A certain aerobic organism is able to metabolize the followingglycolipid CH,OH H H OH H HO OH A.Draw the 2 resulting structures that would occur upon initial hydrolysis of the O-glycosidic bond.arrow_forwardN-NHPH CHO CH2OH H- C=N-NHPH Но- -H- 3 equiv Но- -H- 3 equiv Но- PHNHNH2 PHNHNH, H- H- OH H- -O- H- H- -HO- H- -HO- ČH2OH ČH2OH ČH2OH D-glucose osazone D-fructose + NH3 + PHNH2 + 2 H20 The final step in the formation of the osazone from glucose is the reaction of the keto imine with 2 equivalents of phenylhydrazine to yield the osazone plus ammonia. This reaction involves the following intermediate steps: 1. Addition of phenylhydrazine to the imine and proton transfer to yield intermediate 1; 2. Elimination of ammonia to yield phenylhydrazone 2; 3. Addition of phenylhydrazine to the ketone to yield tetrahedral intermediate 3; 4. Proton transfer yields carbinolamine 4; 5. Elimination of water yields the final product osazone. Write out the mechanism on a separate sh of paper and then draw the structure of tetrahedral intermediate 3. NH НО- -H H- -ОН H- -ОН ОН Glucose keto imine Previous Nearrow_forward
- Write down the reactions: D-Glucose + HNO3 →arrow_forwardOH НО HO OH НО Но OH ОН ОН OH What are the monosachharides that make up this trisaccharide? O a-D-glucopyranose, a-D-galactopyranose, a-D-fructofuranose a-D-glucopyranose, a-D-galactopyranose, B-D-fructofuranose a-D-glucopyranose, a-D-glucopyranose, B-D-fructofuranose a-D-galactopyranose, a-D-glucopyranose, a -D-fructofuranosearrow_forwardDraw the products formed when ß-D-galactose is treated with each reagent.a. Ag2O + CH3Ib. NaH + C6H5CH2Clc. The product in (b), then H3O+d. Ac2O + pyridinee. C6H5COCl + pyridinef. The product in (c), then C6H5COCl + pyridinearrow_forward
- An unknown disaccharide gives a positive Tollens’ test. A glycosidase hydrolyzes it to d-galactose and d-mannose. When the disaccharide is treated with methyl iodide and Ag2O and then hydrolyzed with dilute HCl, the products are 2,3,4,6-tetra-O-methylgalactose and 2,3,4-tri-O-methylmannose. Propose a structure for the disaccharide.arrow_forwardThe following molecule has a glycosidic bond that is best described as HỌ— CH2 НО HO-CH2 НО OH O OH alpha-1,4-glycosidic bond beta-1,6-glycosidic bond alpha-1,6-glycosidic bond beta-1,4-glycosidic bond OH OH OH. H2Oarrow_forwardCellulose, the major structural material of wood and plants, consists of a chain of B-D-glucose molecules connected by B-1,4-glycosidic bonds. In comparison, the amylose component of starch consists of a-D-glucose molecules connected by a-1,4-glycosidic bonds. Identify the following structures, denoted A and B, as the structures of cellulose or amylose. A В 0 Н CH2OH H . н Н OH H Н CH₂OH 0 Н ОН Н ОН Н Н ОН О О Н Н CH₂OH -0 Н OH H Н CH₂OH 0 Н ОН Н ОН Н Н ОН OB is the structure of cellulose, while A is the structure of amylose. O A and B both represent the structure of amylose. O A is the structure of cellulose, while B is the structure of amylose. O A and B both represent the structure of cellulose. Н 0 0 H Н CH₂OH до Н ОН Н Н H OH CH₂OH 0 Н ОН Н Н Н ОН Н О Н H CH₂OH -о Н ОН Н Н ОН CH₂OH 0 H OH HA Н ОН Н H 0arrow_forward
- Identify the type of glycosidic bond in the following disaccharide. CH,OH H H ОН Н CH2 H H H ОН Н HO ОН H. ОН HO H H OH O B-1,4-glycosidic bond O a-1,4-glycosidic bond O B-1,6-glycosidic bond O a-1,6-glycosidic bondarrow_forwardDraw the Fischer projections (D-isomer) of Sorbose and Galactose. Draw the Haworth projections of α-Sorbose and β-Galactose. Draw the structure of β-D-galactopyranosyl-(1→3)-α-D-sorbofuranoside.arrow_forwardDraw the ketohexose provided in the B-pyranose form using the pyranose skeleton as a guide. HO 0: H +OH -HO- Но- -- HO.arrow_forward
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