EBK EXPERIMENTAL ORGANIC CHEMISTRY: A M
6th Edition
ISBN: 9781305687875
Author: Gilbert
Publisher: CENGAGE LEARNING - CONSIGNMENT
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Chapter 9.2, Problem 18E
Interpretation Introduction
Interpretation:
Concept introduction:The presence of double bond between two N atoms as
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(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 4
Draw the structure of the following three isomeric acid chlorides with chemical formula C,H,CIO.
• Use the wedge/hash bond tools to indicate stereochemistry where it exists.
• Consider E/Z stereochemistry of alkenes.
• In cases where there is more than one answer, just give one.
Acid chloride #1: (E)-4-hexenoyl chloride
C P
aste
орy
..."
ChemDoodle
Acid chloride #2: (Z)-3-hexenoyl chloride
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Provide the systematic name for each of the following isomeric esters with the chemical formula C₂H1202.
(Be sure to indicate double bond stereochemistry using (E)/(Z) notation. Indicate stereochemistry in rings with the terms cis or trans. It is not necessary to use italics in writing compound names.)
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(E)-methyl 3-methylpent-3-enoate
An error has been detected in your answer. Check for typos,
miscalculations etc. before submitting your answer.
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isopropyl-2-methylacrylate
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(E)-ethyl pent-2-enoate
12
Chapter 9 Solutions
EBK EXPERIMENTAL ORGANIC CHEMISTRY: A M
Ch. 9.2 - Prob. 1ECh. 9.2 - Prob. 2ECh. 9.2 - Prob. 3ECh. 9.2 - Prob. 4ECh. 9.2 - Prob. 5ECh. 9.2 - Prob. 6ECh. 9.2 - Prob. 7ECh. 9.2 - Prob. 8ECh. 9.2 - Prob. 9ECh. 9.2 - Prob. 10E
Ch. 9.2 - Prob. 11ECh. 9.2 - Prob. 12ECh. 9.2 - Prob. 13ECh. 9.2 - Prob. 14ECh. 9.2 - Prob. 15ECh. 9.2 - Prob. 16ECh. 9.2 - Prob. 17ECh. 9.2 - Prob. 18ECh. 9.2 - Prob. 19ECh. 9.2 - Prob. 20ECh. 9.2 - Prob. 21ECh. 9.2 - Prob. 22ECh. 9.2 - Prob. 23ECh. 9.2 - Prob. 24ECh. 9.3 - Prob. 1ECh. 9.3 - Prob. 2ECh. 9.3 - Prob. 3ECh. 9.3 - Prob. 4ECh. 9.3 - Prob. 5ECh. 9.3 - Prob. 6ECh. 9.3 - Prob. 7ECh. 9.3 - Prob. 8ECh. 9.3 - Prob. 9ECh. 9.3 - Prob. 10ECh. 9.3 - Prob. 11ECh. 9.3 - Prob. 12ECh. 9.3 - Prob. 13ECh. 9.3 - Prob. 14E
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- (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) Ph THF A Ph Ph B H₂SO4 100 °C 3 OH (iii) In analysing both these methods, are there other possible alkene products other than methylenecyclohexane 2? Use mechanistic details to support your answer.arrow_forward3. It is required to introduce a halogen group to a five membered ring, thiophene. Discuss the reaction mechanism involved in the reaction by selecting a suitable halogen group and analyze why a particular substituted product obtained after the reaction is predominant over the other possible product(s) with the help of reactions. To meet the ever increasing demand of global population, the demand for textile products and consumption of dyes by these industries is increasing.arrow_forwardDraw a structural formula for the organic anion (i.e., do not include NH,) formed when benzaldehyde is reacted with Tollens reagent. Don't forget the charge on the ion. - You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. Include all nonzero formal charges.arrow_forward
- When we have discussed the enol-keto tautomerization of ketones in class, the isomerization has been facililated by an acid or base catalyst, with most ketones heavily favoring the carbonyl isomer at equilibrium. However, samples of the ketone below in its pure form (with no acid, base or water present) contain nearly 10% of the enol form! OH -90% -10% From this data, we can infer that the enol isomer of this ketone is particularly stable. Explain the stability of this enol, using terms and ideas that we have discussed in this unit.arrow_forwardDraw the structure of the following three isomeric esters with chemical formula C-H₁2O₂- Ester #1: methyl cyclopentanecarboxylate cyclopropanecarboxylate Ester #2: propyl Ester # 3: ethyl cyclobutanecarboxylate • Consider E/Z stereochemistry of alkenes. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu. **** ChemDoodleⓇ n [F 13arrow_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
- (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_forwardChecking my answer, there was difference with solution. (organic chemistry smith 5th ed 2.47P (d)) Solution said 'the acid base reaction between pentyne and ammonia is product way because pka of pentyne is 25, ammonia is 38 so pentyne will be deprotanted by ammonia.' but I think (and as written in the book) NH4+ is stronger acid than pentyne and acid-base reaction works when reactant is stronger acid than product conjugate acid. It isn't match that pentyne makes NH4+. who is incorrect?arrow_forwardDraw the structural formula of the major product of the reaction of (S)-2,2,3-trimethyloxirane with Me,NH. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Include H atoms at chiral centers only. • If a group is achiral, do not use wedged or hashed bonds on it.arrow_forward
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