ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
10th Edition
ISBN: 9781260028355
Author: Carey
Publisher: MCG CUSTOM
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 21, Problem 62DSP
Interpretation Introduction
Interpretation:
A pair of compounds which is the most reasonable source of all the carbon atoms in the preparation of the given epoxide is to be determined.
Concept Introduction:
Dianion can be prepared from alpha halogenated carboxylic acids by double deprotonation using strong bases such as LDA.
Reaction of dianion of these alpha halogenated carboxylic acids with
In the first step, a new carbon-carbon single bond is formed between the carbonyl carbon of the ketone and the alpha carbon atom of the dianion.
In the second step, the oxygen atom in ketone attacks on the alpha carbon atom of the dianion to form a new carbon-oxygen single bond.
The oxygen atom in the ketone group is a source of oxygen in the
The original
In the process, a carbon-carbon single bond and a carbon-oxygen single bond are formed.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Gg.108.
G.152.
11. See Fundamentals P167 for Figure 5.6
Use Figure 5.6 to rank the compounds in each of the following groups in order
of their reactivity toward electrophilic aromatic substitution:
(a) Nitrobenzene, phenol (hydroxybenzene), toluene
(b) Phenol, benzene, chlorobenzene, benzoic acid
(c) Benzene, bromobenzene, benzaldehyde, aniline (aminobenzene)
Chapter 21 Solutions
ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
Ch. 21.1 - Prob. 1PCh. 21.1 - Prob. 2PCh. 21.1 - Prob. 3PCh. 21.1 - Prob. 4PCh. 21.1 - Prob. 5PCh. 21.2 - Prob. 6PCh. 21.2 - Prob. 7PCh. 21.2 - Prob. 8PCh. 21.3 - Prob. 9PCh. 21.3 - Prob. 10P
Ch. 21.3 - Prob. 11PCh. 21.4 - Prob. 12PCh. 21.4 - Prob. 13PCh. 21.5 - Prob. 14PCh. 21.5 - Problem 21.15 Write the structure of the Dieckmann...Ch. 21.5 - Prob. 16PCh. 21.5 - Prob. 17PCh. 21.6 - Prob. 18PCh. 21.6 - Prob. 19PCh. 21.6 - Prob. 20PCh. 21.6 - Prob. 21PCh. 21.6 - Prob. 22PCh. 21.7 - Prob. 23PCh. 21.8 - Problem 21.24 Mesityl oxide is an industrial...Ch. 21.8 - Prob. 25PCh. 21.8 - Prob. 26PCh. 21.8 - Prob. 27PCh. 21.8 - Prob. 28PCh. 21 - Prob. 29PCh. 21 - Terreic acid, a naturally occurring antibiotic...Ch. 21 - Prob. 31PCh. 21 - Prob. 32PCh. 21 - Prob. 33PCh. 21 - Prob. 34PCh. 21 - Give the structure of the expected organic product...Ch. 21 - Prob. 36PCh. 21 - Prob. 37PCh. 21 - Prob. 38PCh. 21 - Prob. 39PCh. 21 - Give the structure of the principal organic...Ch. 21 - Prob. 41PCh. 21 - Prob. 42PCh. 21 - Prob. 43PCh. 21 - Prob. 44PCh. 21 - Prob. 45PCh. 21 - Prob. 46PCh. 21 - Prob. 47PCh. 21 - The use of epoxides as alkylating agents for...Ch. 21 - Prob. 49PCh. 21 - Show how you could prepare each of the following...Ch. 21 - Prob. 51PCh. 21 - Prob. 52PCh. 21 - Prob. 53PCh. 21 - Prob. 54PCh. 21 - The - methylene ketone sarkomycin has an...Ch. 21 - - Lactone can be prepared in good yield from...Ch. 21 - Prob. 57PCh. 21 - Prob. 58DSPCh. 21 - The Enolate Chemistry of Dianionss The synthetic...Ch. 21 - Prob. 60DSPCh. 21 - Prob. 61DSPCh. 21 - Prob. 62DSPCh. 21 - Prob. 63DSP
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Compounds A, B, and C have the same molecular formula C4H8. They all react wotu H2/PtO2 to give the same compound. The reaction of A or B with H2O/H2SO4 or with BH3-THF, followed by treatment with a basic solution of hydrogen peroxide, gives the same compound, namely D. The reaction of C with H2O/H2SO4 also gives D. However, the reaction of C with BH3-THF, followed by HO-, H2O2 gives a new compound, E. Provide the identity of A, B, C, D, and E along with explanations of reactivity.arrow_forwardThe nitro groups on the benzene ring in the reactant serve two purposes.One is to let you know what atoms in the reactant correspond to what atomsin the product. But what role do the nitro groups play electronically – whywould the reaction be much slower if these nitro groups weren’t attached tothose benzene carbons? Draw any relevant structures to support youranswer.arrow_forwardOo.139. Subject :- Chemistryarrow_forward
- (b) The activating and deactivating groups could affect the position(s) of the next incoming group(s) to the benzene ring. Based on the structure below, analyze and explain the group(s) on the benzene ring is activating or deactivating group. Then, identify the product(s) formed from the following reactions. NH, CC, CH;CH,COCI AICI, (i) NH, HNO, H,SO, (ii) H Br AICI, (iii) Page 3 of 4arrow_forward(a) Give the names of reagents and conditions for each of the reactions I and IIarrow_forward5) 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_forward
- Organic chemistryarrow_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_forwardA benzene ring alters the reactivity of a neighboring group in the so-called “benzylic” position, similarly to how a double bond alters the reactivity of groups in the “allylic” position. Benzylic cations, anions, and radicals are all more stable than simple alkyl intermediates. a) Use resonance structures to show the delocalization of the positive charge, negative charge, and unpaired electron of the benzyl cation, anion, and radical.arrow_forward
- 11.; (a) Similar to alkanes, hydrogen gas can undergo radical bromination according to the reaction below. Propose a chain-reaction mechanism for this reaction, including an initiation step, propagation steps, and two plausible termination steps. The homolytic bond dissociation energy for Br-Br is 46 kcal·mole', for H-Br is 88 kcal'mole and for H-H is 104 kcal'mole'. hv H-H + Br-Br 2 H-Br (b) Calculate the overall AH for the above propagation steps (show all work).arrow_forwardCompound A, C9H16 reacts with 1 molar equivalent(s) of hydrogen upon catalytic hydrogenation. A undergoes reaction with ozone, followed by Zn treatment, to give: 요... CH3CCH₂CH₂CH₂CH₂CH₂CCH3 2CH₂CH₂CH₂CH₂ Propose a structure for A. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. + Submit Answer Try Another Version Sn [F ChemDoodle 2 item attempts remainingarrow_forward(a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) (1) Ph Ph 8*8 Ph THF A 1 Santande B H₂SO4 100 °C 3 OH Using curly arrows, provide full mechanistic details accounting how methylenecyclohexane 2 was synthesised according to both Methods A and B.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning