Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 28, Problem 28.54P
Interpretation Introduction
(a)
Interpretation: The products formed when a given compound is subjected to the Kiliani–Fischer synthesis is to be predicted.
Concept introduction: Kiliani–Fischer synthesis is a method which is used for the elongation of the carbon chains in aldose. In this method, the aldose chain is elongated by the formation of new stereogenic centre at
Interpretation Introduction
(b)
Interpretation: The products formed when a given compound is subjected to the Kiliani–Fischer synthesis is to be predicted.
Concept introduction: Kiliani–Fischer synthesis is a method which is used for the elongation of the carbon chains in aldose. In this method, the aldose chain is elongated by the formation of new stereogenic centre at
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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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- Problem 5.20 Label the two stereogenic centers in dB re stereoisomers. ne. each compound and draw all possible CI a. rro OH Br CI ne b. B. Problem 5.21 Compounds E and F are two isomers of 2,3-dibromopentane drawn in staggered conformations. Which compounds (A-D) in Figure 5.8 are identical to E and F? im et wihr boe A mot Br omin oldne Br F Brarrow_forward12.31 Draw the organic products formed when each compound is treated with H₂, Pd-C. Indicate the three-dimensional structure of all stereoisomers formed. a. b. G d.arrow_forwardProblem 5.23 Which compounds are meso compounds? a. HO "HO, H. OH Он Br C. Br b.arrow_forward
- One step in the synthesis of sitaglipitin (Problem 17.14, a drug used to treat type 2 diabetes) involves reaction of the mixed anhydride A with B to form C. Draw a stepwise mechanism for this reaction.arrow_forwardProblem 5.37 Compare the physical properties of the three stereoisomers of 1,3-dimethylcyclopentane. A B C three stereolsomers of 1,3-dimethylcyclopentane a. How do the boiling points of A and B compare? What about those of A and C? b. Characterize a solution of each of the following as optically active or optically inactive: pure A; pure B; pure C; an equal mixture of A and B; an equal mixture of A and C. c. A reaction forms a 1:1:1 mixture of A, B, and C. If this mixture is distilled, how many fractions would be obtained? Which fractions would be optically active and which would be optically inactive?arrow_forwardProblem 5.2 Classify each pair of compounds as constitutional isomers or stereoisomers. a. and and он 020st geabe AA go Aon e 2o3 С. and d. and b.arrow_forward
- Captopril is a drug used to treat high blood pressure and congestive heart failure. a.Designate each stereogenic center as R or S. b.Draw the enantiomer of captopril. c.What product is formed when captopril is treated with one equivalent of NaH? d.What product is formed when captopril is treated with two equivalents of NaH?arrow_forwardWhat product is formed when a solution of A and B is treated with mild base? This reaction is the rst step in the synthesis of rosuvastatin (sold as a calcium salt under the trade name Crestor), a drug used to treat patients with high cholesterol.arrow_forward60. What reactant will yield this compound when treated with CH3CH2ONA in CH3CH2OH followed by appropriate acid workup? b. d.arrow_forward
- 5.66 A mixture contains equal amounts of compounds A-D. A B C a. Which compounds alone are optically active? b.If the mixture was subjected to fractional distillation, how many fractions would be obtained? c. How many of these fractions would be optically active?arrow_forwardthe carbonyl donor or precursor in the following reaction is: a. A b. B c. C d. NaOHarrow_forwardProblem 5.22 Draw all the possible stereoisomers for each compound, and label pairs of enantiomers hen and diastereomers. Ust a. OH fevidas OH b. CIto snelg e vil OHarrow_forward
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