Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 18, Problem 1LGP
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(b) Complete the following reactions :
(i)
D
H3C
CH3
H
H
كما
.NO2
B
| Bra/Dioxane
.COCH3
A
DHA is a fatty acid derived from sh oil and an abundant fatty acid in vertebrate brains. Hydrogenation of DHA forms docosanoic acid [CH3(CH2)20CO2H] and ozonolysis forms CH3CH2CHO, CH2(CHO)2 (ve equivalents), and HCOCH2CH2CO2H. What is the structure of DHA if all double bonds have the Z conguration?
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When 2-Methylpropene undergoes oxidation in the
presence of acidic K2Cr2O7, the products obtained are
CH3 – CH + CO2
CH3 — СH — С—ОН-СО,
CH, -C =0+CO2 +H2O
CH3
CH; – CH2 – CH + CO2 + H20
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Chapter 18 Solutions
Organic Chemistry
Ch. 18 - Prob. 1PPCh. 18 - Practice Problem 18.2 Would optically active...Ch. 18 - Prob. 3PPCh. 18 - Practice Problem 18.4 Why do we say that the...Ch. 18 - Prob. 5PPCh. 18 - Practice Problem 18.6 (a) Write a reaction...Ch. 18 - PRACTICE PROBLEM 18.7
Show how you would use the...Ch. 18 - Practice Problem 18.8 The acetoacetic ester...Ch. 18 - Practice Problem 18.9
In the synthesis of the keto...Ch. 18 - PRACTICE PROBLEM 18.10 How would you use the...
Ch. 18 - PRACTICE PROBLEM 18.11
How would you use the...Ch. 18 - PRACTICE PROBLEM 18.12 Outline all steps in a...Ch. 18 - PRACTICE PROBLEM 18.13
The antiepileptic drug...Ch. 18 - PRACTICE PROBLEM 18.14 Show how you could employ...Ch. 18 - Prob. 15PCh. 18 - Treating a solution of cis-1-decalone with base...Ch. 18 - Prob. 17PCh. 18 - Prob. 18PCh. 18 - Prob. 19PCh. 18 - Prob. 20PCh. 18 - Prob. 21PCh. 18 - Prob. 22PCh. 18 - Prob. 23PCh. 18 - The synthesis of cyclobutanecarboxylic acid given...Ch. 18 - Prob. 25PCh. 18 - Prob. 26PCh. 18 - Prob. 27PCh. 18 - Prob. 28PCh. 18 - Compound J, a compound with two four-membered...Ch. 18 - Prob. 30PCh. 18 - Prob. 31PCh. 18 - 18.32 Shown below is a synthesis of the elm bark...Ch. 18 - 18.33 (a) A compound U gives a negative iodoform...Ch. 18 - 18.34 Compound A has the molecular formula and...Ch. 18 - Prob. 35PCh. 18 - Prob. 36PCh. 18 - Prob. 37PCh. 18 - Prob. 38PCh. 18 - 1. -Carotene is a highly conjugated hydrocarbon...Ch. 18 - Dehydroabietic acid is a natural product isolated...
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- 5. Consider the synthesis of 2-butanone from butyne: Hg2+ CH3CH,-C=C–H CH3CH, Ĉ -CH3 H3o* (i) Draw the structure of the compound D. (ii) Compound D isomerizes to form 2-butanone. What is this isomeric process called? (iii) Use the mechanism to show the conversion of compound D to 2-butanone.arrow_forward(10pts) Compound A, C10H16, was found to be optically active. On catalytic reduction over a palladium catalyst, 2 equivalents of hydrogen were absorbed, yielding compound B, CioH2o. On ozonolysis of A, two fragments were obtained. One fragment was identified as acetic acid (CHCOOH). The other fragment, compound C, was an optically active carboxylic acid, C8H14O2. Write reactions, and draw the correct structures for A-C, explain your answer in detail.arrow_forwardProteases are enzymes that can break covalent bonds in proteins. Proteases play major roles in the regulation of biological processes, so compounds that inhibit their function, called protease inhibitors, have potential as therapeutic agents. While preparing several potential protease inhibitors, compound 1 was converted into compound 3 via alkyne 2, as shown. (J. Org. Chem. 1989, 54, 3963- 3972) Draw the structure of alkyne 2, and propose reagents for converting 1 into 3. Step 1 Br Br Ph alle Br Br Edit Drawing OH Modify the given structure of 1 to draw alkyne 2. An eraser is available, and you can use the single bond tool to add/remove pi bonds. OH 2 Ph O ell (-10) Ph = 3 OHarrow_forward
- 5) Limonene is a compound found in orange oil and lemon oil with molecular formula C₁0H16- When limonene is treated with 1 equivalent of mCPBA, the product is limonene oxide as depicted below. When limonene is treated with excess ozone (03) and then with dimethylsulfide (Me₂S), one of the organic products of the reaction is formaldehyde. Of the structures below, which correspond to the structure of limonene and/or the structure of the other major organic product when limonene is reacted with O3 and Me₂S? Please select any and all that apply. A) 'Н H B) ? H 1) 03 (XS) 2) Me₂S (xs) ? limonene, C10H16 D) mCPBA (1 equiv) E) limonene oxide None of the abovearrow_forwarda) When (Z)-3-methylhex-3-ene undergoes hydroboration–oxidation, two isomeric products are formed. Give their structures, and label each asymmetric carbon atom as (R) or (S). What is the relationship between these isomers?arrow_forward(a) Answer the following questions based on the reaction scheme below. Jawab soalan berikut berdasarkan rajah tindak balas di bawah. H,SO, 180°C R OH+ Δ U NH, (i) State reagent Q. Nyatakan reagen Q. (ii) Draw the structural formula for compounds R, T, U and W. Lukiskan formula struktur bagi sebatian R, T, U dan W. PCI,arrow_forward
- Compound W has molecular formula C₁4H18 and reacts with H₂ to form X. Oxidative cleavage of W with O3 followed by CH3 SCH3 affords Y. What is the structure of W?arrow_forwardChlordane, like DDT, is an alkyl halide that was used as an insecticide for crops such as corn and citrus and for lawns. In 1983, it was banned for all uses except against termites, and in 1988, it was banned for use against termites as well. Chlordane can be synthesized from two reactants in one step. One of the reactants is hexachlorocyclopentadiene. What is the other reactant?arrow_forward5. Consider the synthesis of 2-butanone from butyne: Hg2+ || CH3CH,-C=C–H CH;CH,-Ĉ-CH3 H3o* (iv) Name the class of compound D belongs to. (v) Comment on the stability of compound D compared to 3-butanone.arrow_forward
- Give reasons: (i) C—Cl bond length in chlorobenzene is shorter than C—Cl bond length in CH3—Cl.(ii) The dipole moment of chlorobenzene is lower than that of cyclohexyl chloride.(iii) SN1 reactions are accompanied by racemization in optically active alkyl halidesarrow_forward(a) Account for the following :(i) Electrophilic substitution reactions in haloarenes occur slowly.(ii) Haloalkanes, though polar, are insoluble in water.(b) Arrange the following compounds in increasing order of reactivity towards SN2 displacement:2-Bromo-2-Methylbutane, 1-Bromopentane, 2-Bromopentanearrow_forwardC12T04Q8272 Give the major product(s) of the following reaction. CrO3 он H,SO4 H. of HO, OMe HO. There is no reaction under these conditions or the correct product is not listed here.arrow_forward
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Chapter 4 Alkanes and Cycloalkanes Lesson 2; Author: Linda Hanson;https://www.youtube.com/watch?v=AL_CM_Btef4;License: Standard YouTube License, CC-BY
Chapter 4 Alkanes and Cycloalkanes Lesson 1; Author: Linda Hanson;https://www.youtube.com/watch?v=PPIa6EHJMJw;License: Standard Youtube License