ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
12th Edition
ISBN: 9781119304241
Author: Solomons
Publisher: WILEY C
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Textbook Question
Chapter 8, Problem 3PP
Practice Problem 8.3
Provide mechanistic explanations for the following observations:
(a)
(b)
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Provide the reagents and solvents (where appropriate) needed to bring about the following
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(a)
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PRACTICE PROBLEM 8.20
Specify the alkene and reagents needed to synthesize each of the following diols.
OH
HO-
(a)
(b)
(c)
HO.
н он
HO
(racemic)
(racemic)
2. (18pts) (a) Draw bond-line structures and include appropriate wedge and dash notation for the following
compounds. (b) Identify each pair that would be optically inactive as a 50/50 mixture. (c) Identify pair of
compounds that represent diastereomers.
H
H
A
Br
Br
Br
H
B
Br
Br
H-Et
H
Br
C
Br
Br
CH3
D
H
H
Chapter 8 Solutions
ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
Ch. 8 - Prob. 1PPCh. 8 - Prob. 2PPCh. 8 - Practice Problem 8.3 Provide mechanistic...Ch. 8 - Prob. 4PPCh. 8 - Prob. 5PPCh. 8 - Prob. 6PPCh. 8 - Prob. 7PPCh. 8 - Prob. 8PPCh. 8 - Prob. 9PPCh. 8 - Prob. 10PP
Ch. 8 - Prob. 11PPCh. 8 - Prob. 12PPCh. 8 - Practice Problem 8.13
Specify the appropriate...Ch. 8 - Prob. 14PPCh. 8 - Practice Problem 8.15 Write a mechanism to explain...Ch. 8 - Prob. 16PPCh. 8 - Prob. 17PPCh. 8 - Prob. 18PPCh. 8 - Practice Problem 8.19 Treating cyclohexene with l,...Ch. 8 - Prob. 20PPCh. 8 - Practice Problem 8.21
Predict the products of the...Ch. 8 - Prob. 22PPCh. 8 - Prob. 23PPCh. 8 - Prob. 24PPCh. 8 - Prob. 25PPCh. 8 - Write structural formulas for the products that...Ch. 8 - Prob. 27PCh. 8 - Prob. 28PCh. 8 - 8.29. Give the structure of the products that you...Ch. 8 - Give the structure of the products you would...Ch. 8 - Prob. 31PCh. 8 - Prob. 32PCh. 8 - Prob. 33PCh. 8 - Prob. 34PCh. 8 - Prob. 35PCh. 8 - Prob. 36PCh. 8 - Prob. 37PCh. 8 - When 3, 3-dimethyl-2-butanol is neared with...Ch. 8 - Prob. 39PCh. 8 - Prob. 40PCh. 8 - Prob. 41PCh. 8 - Prob. 42PCh. 8 - 8.43. Write a mechanism that explains the...Ch. 8 - 8.44. Write a mechanism for the following...Ch. 8 - Write a mechanism that explains formation of the...Ch. 8 - Prob. 46PCh. 8 - 8.47. Farnesene (below) is a compound found in the...Ch. 8 - Limonene is a compound found in orange oil and...Ch. 8 - Prob. 49PCh. 8 - Synthesize the following compound starting with...Ch. 8 - Predict features of their IR spectra that you...Ch. 8 - Deduce the structures of compounds A, B, and C,...Ch. 8 - Ricinoleic acid, a compound that can be isolated...Ch. 8 - 8.54. There are two dicarboxylic acids with the...Ch. 8 - Prob. 55PCh. 8 - Prob. 56PCh. 8 - Prob. 57PCh. 8 - Prob. 58PCh. 8 - 8.59. For each of the following questions, please...Ch. 8 - Prob. 60PCh. 8 - Prob. 61PCh. 8 - Prob. 62PCh. 8 - Triethylamine, (C2H5)3N, like all amines, has a...Ch. 8 - (a) Synthesize (3S, 4R)-3,...Ch. 8 - Prob. 2LGPCh. 8 - Prob. 3LGPCh. 8 - Prob. 4LGP
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- . (a) 2,5-Dimethyl-1,1- cyclopentanedicarboxylic acid (I) may be prepared as two optically inactive substances (A and B) of different m.p. Draw their possible structures. (b) Upon heating, A yields two 2,5- dimethylcyclopentanecarboxylic acid structures (II), and B yields only one. Assign structures to A and B. HO2C Co 2H HO 2C, Harrow_forwardExplain the following behaviours :(i) Alcohols are more soluble in water than the hydrocarbons of comparable molecular masses.(ii) Ortho-nitrophenol is more acidic than ortho-methoxyphenol.arrow_forwardPractice Problem 17.30 Write the number of A electrons for the following compound. Number of A electrons: exact number, no tolerancearrow_forward
- Compound A has prominent infrared absorptions at 1050, 1786, and 1852 cm and shows a single absorption in the proton NMR spectrum at 8 3.00. When heated gently with methanol, compound B, C,H,O,, is obtained. Compound B has IR absorptions at 2500–3000 (broad), 1730, and 1701 cm-, and its proton NMR spectrum in D,0 consists of resonances at & 2.7 (complex splitting) and & 3.7 (a singlet) in the intensity ratio 4:3. Give the structures A and B, omitting stereochemistry.arrow_forward13. (a) Compound C undergoes a reaction with SOC1₂ (or PC15) to yield compound D (Molecular Formula C₁0H₁0OCIBr) which has the following spectral data: Compound D: IR: 1685 cm¹; ¹H NMR: 8 7.84 (d, J = 8 Hz, 2H), 7.60 (d, J=8 Hz, 2H), 3.65 (t, J = 7 Hz, 2H), 3.18 (t, J = 7 Hz, 2H), 2.25 (pentet, J = 7 Hz, 2H) ppm; ¹3C NMR: d 28, 36, 45, 128, 130, 133, 137, 197 ppm; EI MS m/z: 200, 198(1:1), 185, 183 (1:1). Identify compound C from the spectral data of compound B and justify your observation. (b) Differentiate between the following: i) COSY and NOESY ii) COSY 90 and COSY 45arrow_forward2. DEDUCE THE STRUCTURE FOR EACH COMPOUND WITH THE INDICATED MOLECULAR FORMULA AND THE 1H-NMR AND IR SPECTRA PROVIDED. (a) Formula: C4H8O2arrow_forward
- 8.1)The enol content of CH3COCH2CO2Et in hexane is 46% and that in water is 0.4%. Thereason for the above observation is as follows: (A) Intermolecular hydrogen bonding is stabilized by hexane. (B) Intramolecular hydrogen bonding is stabilized by water. (C) Intramolecular hydrogen bonding is destabilized by water. (D) CH3COCH2CO2Et dissolves in hexane completely. 2)The molecular formula of glucose is C6H12O6. The chemical composition of glucose is(A) 39.99 % C, 6.71 % H, 53.27 % O (B) 40.99 % C, 6.71 % H, 53.27 % O(C) 39.99 % C, 7.71 % H, 54.27 % O (D) 29.99 % C, 7.71 % H, 53.00 % O 3)20 mL of 0.2 M hydrochloric acid is added to 5 mL of 0.1 M sodium carbonate. Theresultant solution is then titrated against 0.2 M sodium hydroxide. What will be the titrevalue?(A) 15 mL (B) 10 mL (C) 5 mL (D) 20 mL 4) High thermal stabilities of transition metal carbonyls are due to- (A) non-availability of d-orbital on carbon. (B) formation of an ionic bond between CO and metal. (C) interaction of…arrow_forwardTreatment of compound E (molecular formula C4H8O2) with excessCH3CH2MgBr yields compound F (molecular formula C6H14O) afterprotonation with H2O. E shows a strong absorption in its IR spectrum at1743 cm−1. F shows a strong IR absorption at 3600−3200 cm−1. The 1HNMR spectral data of E and F are given. What are the structures of E andF?Compound E signals at 1.2 (triplet, 3 H), 2.0 (singlet, 3 H), and 4.1 (quartet, 2 H) ppm Compound F signals at 0.9 (triplet, 6 H), 1.1 (singlet, 3 H), 1.5 (quartet, 4H), and 1.55 (singlet, 1 H) ppmarrow_forward13. (a) Compound C undergoes a reaction with SOC12 (or PCls) to yield compound D (Molecular Formula C₁0H₁0OCIBr) which has the following spectral data: Compound D: IR: 1685 cm¹; ¹H NMR: 8 7.84 (d, J = 8 Hz, 2H), 7.60 (d, J = 8 Hz, 2H), 3.65 (t, J = 7 Hz, 2H), 3.18 (t, J = 7 Hz, 2H), 2.25 (pentet, J = 7 Hz, 2H) ppm; ¹³C NMR: d 28, 36, 45, 128, 130, 133, 137, 197 ppm; EI MS m/z: 200, 198(1:1), 185, 183 (1:1). Identify compound C from the spectral data of compound B and justify your observation.arrow_forward
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