Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 17.10, Problem 12P
Problem
Classify the bromohydrins formed from cis- and trans-
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Problem
19.22 Show how ethyl bromide can be used as a starting material in the preparation of each of the
following compounds. (Hint: How are Grignard reagents prepared?)
HO
`CH;CH3
(a)
OH
(b)
OH
(c) 1-butanol
(d)
PHCHCH,CH;
(CH;CH;),CCH3
Problem 16.33
What steps are needed to convert benzene to p-isobutylacetophenone, a synthetic
intermediate used in the synthesis of the anti-inflammatory agent ibuprofen.
ive
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17.41
Draw the products of each reduction reaction.
NABH4
а.
CH3OH
[1] LIAIH4
[2] H2O
HO
[1] LIAIHĄ
С.
[2] H2O
b.
Chapter 17 Solutions
Organic Chemistry - Standalone book
Ch. 17.1 - Prob. 1PCh. 17.2 - The heats of combustion of 1, 2-epoxybutane...Ch. 17.3 - Prob. 3PCh. 17.4 - Prob. 4PCh. 17.5 - Prob. 5PCh. 17.6 - Problem 17.6 (a) Write equations describing two...Ch. 17.6 - Problem 17.7 Only one combination of alkyl halide...Ch. 17.6 - Prob. 8PCh. 17.8 - Prob. 9PCh. 17.8 - Prob. 10P
Ch. 17.9 - Prob. 11PCh. 17.10 - Problem 17.12 Classify the bromohydrins formed...Ch. 17.11 - Prob. 13PCh. 17.11 - Prob. 14PCh. 17.12 - Prob. 15PCh. 17.12 - Prob. 16PCh. 17.14 - Prob. 17PCh. 17.15 - Prob. 18PCh. 17.16 - Prob. 19PCh. 17.17 - Problem 17.20 There is another oxygen-stabilized...Ch. 17 - Prob. 21PCh. 17 - Many ethers, including diethyl ether, are...Ch. 17 - Although epoxides are always considered to have...Ch. 17 - The name of the parent six-membered...Ch. 17 - Prob. 25PCh. 17 - Prob. 26PCh. 17 - Prob. 27PCh. 17 - Prob. 28PCh. 17 - Prob. 29PCh. 17 - Given that: does the product of the analogous...Ch. 17 - Prob. 31PCh. 17 - Prob. 32PCh. 17 - Prob. 33PCh. 17 - Prob. 34PCh. 17 - Prob. 35PCh. 17 - Prob. 36PCh. 17 - When (R)-(+)-2-phenyl-2-butanol is allowed to...Ch. 17 - Prob. 38PCh. 17 - Prob. 39PCh. 17 - Write a mechanism for the following reaction.Ch. 17 - Prob. 41PCh. 17 - Prob. 42PCh. 17 - Prob. 43PCh. 17 - Prob. 44PCh. 17 - Prob. 45PCh. 17 - Prob. 46DSPCh. 17 - Prob. 47DSPCh. 17 - Prob. 48DSPCh. 17 - Prob. 49DSPCh. 17 - Epoxide Rearrangements and the NIH Shift This...Ch. 17 - Epoxide Rearrangements and the NIH Shift This...
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- Problem 13.28 What reagent is needed to convert (CH3)2CHCH₂ COCI to each compound? a. b. C. d. но Ho ГОНarrow_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_forward25.38 Draw the product of each intramolecular cycloaddition. а. hv [2 + 2] b. A [4 + 2] OSIR3 с. A [6 + 4] d. hv [2 + 2] Rage 11arrow_forward
- 17.43 Draw the products of each reduction reaction. NaBH4 CH3OH OH [1]LIAIH [2] H₂O [1]LIAIH4 OH d. CI [2] H₂O [1]LIAIH[OC(CH3)33 [2] H₂Oarrow_forwardBromoetherification, the addition of the elements of Br and OR to adouble bond, is a common method for constructing rings containingoxygen atoms. This reaction has been used in the synthesis of thepolyether antibiotic monensin (Problem 18.34). Draw a stepwisemechanism for the following intramolecular bromoetherification reaction.arrow_forwardDraw the product of each Diels-Alder reaction and indicate the stereochemistry at all stereogenic centers. A a. b.arrow_forward
- Problem 5.27 (a) Label the four stereogenic centers in sorbitol as R or S. (b) How are sorbitol and A related? (c) How are sorbitol and B related? HO H HO H но н но н Н Он Н ОН HO HO но но но н он Н ОН B H OH HO H HO H HO H sorbitol Aarrow_forwardWhich heterocycles are aromatic? a. d. b.arrow_forwardDraw the structure and include stereochemistryarrow_forward
- Bromoetherification, the addition of the elements of Br and OR to a double bond, is a common method for constructing rings containing oxygen atoms. This reaction has been used in the synthesis of the polyether antibiotic monensin (Problem 18.34). Draw a stepwise mechanism for the following intramolecular bromoetherification reaction.arrow_forwardProblem 13.34 Synthesize each compound from cyclohexanol, ethanol, and any other needed reagents. a. b. C. d. e. OH XOH Br OHarrow_forwardProblem 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_forward
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