EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Textbook Question
Chapter 6.10, Problem 28P
What
- a. 24 propyloxirane
- b. cyclohexene oxide
- c. 2,2,3,3-tetramethyloxirane
- d. 2,3-cpoxy-24methylpentane
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consider the followving reaction of a carbonyl to an alkene
"CH2
P-Ph
Ph Ph
CH2
Phosphonium ylide
What is the name of the reaction that converts carbonyls to alkenes?
a. Witten Reaction
b. Wittig Reaction
c. Welker Reaction
d. Whinging Reaction
What steps are needed to generate the phosphonium ylide?
a. Triphenylphosphine + CH,I – Treat with NaH
b. Treat with NaH – Triphenylphosphine + CH;I
c. Triphenylphosphine + CH, - Treat with NaOH
d. Treat with NaOH – Triphenylphosphine + CH,
Can you explain the reasons and concepts for why these answers are true?
What is the major product of the reaction of 1 mol of propyne with each of the following reagents?
a. HBr (1 mol) e. aqueous H2SO4, HgSO4 h. H2/Lindlar catalyst
b. HBr (2 mol) f. R2BH in THF followed by i. sodium amide
c. Br2 (1 mol)/CH2Cl2 H2O2/HO-/H2O j. the product of part i followed by
d. Br2 (2 mol)/CH2Cl2 g. excess H2, Pd/C 1-chloropropane
Chapter 6 Solutions
EBK ORGANIC CHEMISTRY
Ch. 6.1 - Draw the mechanism for the reaction of cyclohexene...Ch. 6.2 - a. How many bond orbitals are avilable for...Ch. 6.2 - Prob. 3PCh. 6.2 - Prob. 4PCh. 6.3 - Prob. 5PCh. 6.4 - Prob. 6PCh. 6.4 - Prob. 7PCh. 6.4 - What alkene should be used to synthesize each of...Ch. 6.5 - The pKa of a protonated alcohol is about 2.5, and...Ch. 6.5 - Prob. 10P
Ch. 6.5 - Prob. 11PCh. 6.6 - a. What is the major product or each or the...Ch. 6.6 - Prob. 14PCh. 6.6 - Prob. 15PCh. 6.7 - What is the major product obtained from the...Ch. 6.8 - Which is more highly regionselective: reaction of...Ch. 6.8 - Prob. 19PCh. 6.9 - What will be the product of the preceding reaction...Ch. 6.9 - Prob. 21PCh. 6.9 - Prob. 22PCh. 6.9 - Prob. 23PCh. 6.9 - What is the product of the addition of 1Cl to...Ch. 6.9 - What will be the major product obtained from the...Ch. 6.9 - Propose a mechanism for the following reaction:Ch. 6.10 - Draw structures for the following: a. 24...Ch. 6.10 - What alkene would you treat with a peroxyacid in...Ch. 6.11 - What products are formed when the following...Ch. 6.11 - Prob. 31PCh. 6.11 - Prob. 32PCh. 6.11 - The following product was obtained from the...Ch. 6.12 - What characteristics must the reactant of a...Ch. 6.13 - Prob. 36PCh. 6.13 - What stereoisomers are obtained from each of the...Ch. 6.13 - Prob. 41PCh. 6.13 - Prob. 42PCh. 6.13 - Prob. 43PCh. 6.13 - Prob. 45PCh. 6.13 - Prob. 46PCh. 6.13 - Prob. 47PCh. 6.13 - Prob. 48PCh. 6.13 - Prob. 49PCh. 6.13 - Prob. 50PCh. 6.14 - Prob. 51PCh. 6.16 - Prob. 53PCh. 6.16 - Explain why 3-methykyclohexene should not be used...Ch. 6 - Prob. 55PCh. 6 - Prob. 56PCh. 6 - Prob. 57PCh. 6 - What is the major product of the reaction of...Ch. 6 - Give two names for each of the following:Ch. 6 - Prob. 60PCh. 6 - What are the products of the following reactions?...Ch. 6 - When 3-methyl-1-butene reacts with HBr, two alkyl...Ch. 6 - Draw curved arrows to show the flow of electrons...Ch. 6 - What reagents are needed to carry out the...Ch. 6 - Prob. 65PCh. 6 - Prob. 66PCh. 6 - Prob. 67PCh. 6 - What is more stable? a. CH3C+HCH3orCH3C+HCH2ClCh. 6 - Prob. 69PCh. 6 - a. Draw the product or products that will be...Ch. 6 - Prob. 71PCh. 6 - The second-order rate constant (in units of M1s1)...Ch. 6 - Which compound has the greater dipole moment?Ch. 6 - Prob. 74PCh. 6 - Prob. 75PCh. 6 - Prob. 76PCh. 6 - Prob. 77PCh. 6 - Prob. 78PCh. 6 - Prob. 79PCh. 6 - Prob. 80PCh. 6 - Prob. 81PCh. 6 - Prob. 82PCh. 6 - Prob. 83PCh. 6 - Prob. 84PCh. 6 - Prob. 85PCh. 6 - Prob. 86PCh. 6 - Draw the products of the following reactions. If...Ch. 6 - Prob. 88PCh. 6 - Prob. 89PCh. 6 - Prob. 90PCh. 6 - Two chemists at Dupont found that lCH2Znl is...Ch. 6 - Prob. 92PCh. 6 - Prob. 93PCh. 6 - What alkene gives the product shown after...Ch. 6 - Prob. 95PCh. 6 - Prob. 96PCh. 6 - Prob. 97PCh. 6 - Prob. 98PCh. 6 - Prob. 99PCh. 6 - Prob. 100PCh. 6 - Propose a mechanism for the following reaction:Ch. 6 - Prob. 102PCh. 6 - Prob. 103P
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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
- 1. What alkene will produce the HIGHEST yield of the alkyl halide below? 2. Which of the following alkynes can be deprotonated by NaNH2 in liquid NH3? a. Pent-2-yne b. Hex-3-yne c. none of these d. 3-Methylbutyne e. 3-Methylhex-2-ynearrow_forwardWhich of the following reagents will produce aldehydes from ethylene? O A. hot, acidic KMNO4 B. Os04 in NaHSO4 O c. 03, Zn and H20 D. H+/H2Oarrow_forwardThese reagents can produce ketones with alkynes A. BH3, THF, H2O2 B. KMnO4 C. O3 D. H2SO4, H2O, HgSO4arrow_forward
- What stereoisomers are formed in the following reactions? Which stereoisomer is the major product? a. the acid-catalyzed dehydration of 1-pentanol to 2-pentene b. the acid-catalyzed dehydration of 3,4-dimethyl-3-hexanol to 3,4-dimethyl-3-hexenearrow_forward21. Provide the reagents necessary to carry out the following reaction. following conversion. CN 22. Provide the reactant for the NH₂ Ph3P=CHCH3 A. B. ܘܘܣ C. D. cyclohexanone cyclohexanecarbaldehyde cyclohexylpropanone 3-cyclohexylpropanalarrow_forward43. Identify the reagent that will produce the following brominated product in greatest amount. Br A. Br2/uv B. Br2/FeBr3 C. NBS D. B12/CC14 44. Under acidic condition, which of the following compounds can not be oxidized by KMnO4. A. toluene B. 2-butene C. methylcyclohexane D. 2-butyne 45. What alkene product can be produced from the reaction of 2-hexyne with Lindlar's catalyst? A. cis-2-Hexene B. trans-2-Hexene C. Hexane D. A and Barrow_forward
- What is the best set of reagents to achieve deoxygenation of 2-pentanone to pentane? A. NaClO2/NaH2PO4 B. LiAlH4, Et2O C. DIBAL-H, THF D. NH2NH2/t-BuOK, DMSOarrow_forwardNitration of chlorobenzene gives A. o - chloronitrobenzene B. p - chloronitrobenzene C. m – chloronitrobenzene D. A and B BO DO CO A Oarrow_forward51. Which of the following reactants can be used in the synthesis of 1-butanamine 1. LiAIH4 ? 2. H2O I. 2 CH3CH₂COCH₂CH3 I. П. CN Ш. A. I and II only B. II and III only C. I and III only 52. What is the major product of the following condensation reaction? A.I ОН II. NH₂ ОН 1.CH3CH2O 2. Н30 Jackson ČOCH₂CH3 CN III. ? CH3CH₂CHCHCOCH₂CH3 IV. CH3CH₂CCH₂CH₂COCH₂CH3 CH3 NH 0 V. CH₂CH₂CCHCOCH₂CH3 CH3 CH3CH₂CHCH₂CH₂COCH₂CH₂ В. ІІ С. III D. IV E. V D. I,II, and IIIarrow_forward
- For each of the reactions indicate which reactant is the nucleophile and which is the electrophile.arrow_forward4. Which of the following reactions is NOT a method of preparation of alkylhalide? A. addition of halogens to alkenes B. replacement of the -OH in alcohol by a halide C. dehydrohalogenation of hydrocarbon D. addition of hydrogen halide to alkene 5. In SN₂ reaction of alkylhalide(substrate) with NaOH(nucleophile), the rate of the reaction is tripled if the concentration of: A. Substrate and nucleophile are both doubled B. Nucleophile is decreased by 1/3 and substrate doubled C. Substrate is tripled and nucleophile doubled D. Nucleophile is tripled 6. Arrange the following alkylhalide in order of decreasing reactivity in an SN₁ reaction: I. CH3CH(Br)CH₂CH3 A. I>II>III>IV II. CH3CH(C1)CH₂CH3 III. CICH₂CH₂CH₂CH3 IV. (CH3)2C(Br)CHCH3 D. IV>II>I>III B. IV>III>II>I C. IV>I>II>IIIarrow_forward62. What are the possible products in Claisen condensation reaction. A. Beta hydroxyl ketone and an alcohol B. Beta hydroxyl ketone and a ketone C. Beta keto ester and an alcohol D. Beta keto ester and a ketone For Nos. 63-70 Choose: A -if the indicated property/behavior in item I is greater than in item II B-if the indicated property/behavior in item I is less than in item II. C- if the indicated property/behavior is equal in item I and item II. D- if the indicated data is insufficient to make a comparison.arrow_forward
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How to Design a Total Synthesis; Author: Chemistry Unleashed;https://www.youtube.com/watch?v=9jRfAJJO7mM;License: Standard YouTube License, CC-BY