Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
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Chapter 5, Problem 61P
Interpretation Introduction
Interpretation: The flow chart of the resolution of the racemic 2-hydroxypropanoic needs to be determined.
Concept Introduction:Bromoniation is a process in which bromine atom reacts with the compound and replaces the hydrogen atom.
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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
Determine product (A) of the reaction
(1)
NK + DMF
CH2 – Br
(A)
(81%)
(2) HO¯/H2O
(Benzyl bromide)
(a) Ph – NH2
(c) Ph – CH2 – NH – CO,H
(b) Ph – CH2 – NH2
(d) Ph – CH, - NH – CHO
Which of the following reactions will synthesize phenol from benzene?
1) HNO3 + H2SO4; 2) Fe, HCl; 3) NaNO2, HCl, 0-10 oC; 4) warm H2SO4 and H2O
1) HNO3 + H2SO4; 2) Fe, HCl; 3) NaNO2, HCl, 0-10 oC; 4) CuCN; 5) dilute acid and heat
1) Acetyl chloride & AlCl3; 2) bleach
1) Ph-N2+ + KI; 2) BrMgCH=CH2 in ether, followed by H3O+; 3) warm, conc'd KMnO4
1) Cl-CH(CH3)-CH2CH2CH3 + FeBr3; 2) hot, conc'd KMnO4
Chapter 5 Solutions
Organic Chemistry: Structure and Function
Ch. 5.1 - Prob. 5.3ECh. 5.1 - Prob. 5.4ECh. 5.1 - Prob. 5.5ECh. 5.2 - Prob. 5.6ECh. 5.2 - Prob. 5.8TIYCh. 5.3 - Prob. 5.9ECh. 5.3 - Prob. 5.11TIYCh. 5.3 - Prob. 5.12ECh. 5.4 - Prob. 5.13ECh. 5.4 - Prob. 5.14E
Ch. 5.4 - Prob. 5.16TIYCh. 5.4 - Prob. 5.17ECh. 5.5 - Prob. 5.18ECh. 5.5 - Prob. 5.19ECh. 5.5 - Prob. 5.20ECh. 5.6 - Prob. 5.21ECh. 5.6 - Prob. 5.22ECh. 5.6 - Prob. 5.23ECh. 5.7 - Prob. 5.24ECh. 5.7 - Prob. 5.26TIYCh. 5.7 - Prob. 5.27ECh. 5 - Prob. 5.1ECh. 5 - Prob. 5.2ECh. 5 - Prob. 30PCh. 5 - Prob. 31PCh. 5 - Prob. 32PCh. 5 - Prob. 33PCh. 5 - Prob. 34PCh. 5 - Prob. 35PCh. 5 - Prob. 36PCh. 5 - Prob. 37PCh. 5 - Prob. 38PCh. 5 - Prob. 39PCh. 5 - Prob. 40PCh. 5 - Prob. 41PCh. 5 - Prob. 42PCh. 5 - Prob. 43PCh. 5 - Prob. 44PCh. 5 - Prob. 45PCh. 5 - Prob. 46PCh. 5 - Prob. 47PCh. 5 - Prob. 48PCh. 5 - Prob. 49PCh. 5 - Prob. 50PCh. 5 - Prob. 51PCh. 5 - Prob. 52PCh. 5 - Prob. 53PCh. 5 - Prob. 54PCh. 5 - Prob. 55PCh. 5 - Prob. 56PCh. 5 - Prob. 57PCh. 5 - Prob. 58PCh. 5 - Prob. 59PCh. 5 - Prob. 60PCh. 5 - Prob. 61PCh. 5 - Prob. 62PCh. 5 - Prob. 63PCh. 5 - Prob. 64PCh. 5 - Prob. 65PCh. 5 - Prob. 66PCh. 5 - Prob. 67PCh. 5 - Prob. 68PCh. 5 - Prob. 69PCh. 5 - Prob. 70PCh. 5 - Prob. 71P
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- Help ASAP Illustrate the resonance effect of the methoxy group -OCH3, on the structure of the benzene ring. Do this by writing all the possible resonance forms for methoxybenzene, including the hybrid. Based on your structures, explain how the presence of the -OCH3 group affects: (i) the reactivity of the benzene ring towards electrophilic attack; (ii) the orientation or point of attack of an incoming electrophilic reagent on the benzene ring.arrow_forwardSpecialized reagents and their acronyms: MCPBA= meta-chloroperbenzoic acid; HOAC = acetic acid, NaOAc = Sodium Acetate; Ph= phenyl = C6H5-; P(Ph)3 = triphenyl phosphine; NBS = N- bromosuccinimide, PBR3, SOCI2, AlCl3, FeBr3, H2SO4, Li, Na, Mg, Br2, CrO3, LDA = lithium diisopropylamide, PCC = pyridinium chlorochromate, KO-C(CH3)3, LAH = LIAIH4, (sia)2BH = disecondary isobutyl borane, KMNO4, HIO4 = periodic acid %3D %3D %3D %3D %3D write the missing reagents and solvents over the arrows. Some transformation require multiple steps. In some cases there will be multiple arrows. Br Brarrow_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. H H;C-C-c CH, Br AIC13 NH, so, H,SO4 (ii) NH, Hfos CH;C1 AICI, (iii)arrow_forward
- Specialized reagents and their acronyms: MCPBA= meta-chloroperbenzoic acid; HOAC = acetic acid, NaOAc = Sodium Acetate; Ph= phenyl = C6H5-; P(Ph)3 = triphenyl phosphine; NBS = N- bromosuccinimide, PBR3, SOCI2, AICI3, FeBr3, H2SO4, Li, Na, Mg, Br2, CrO3, LDA = lithium diisopropylamide, PCC = pyridinium chlorochromate, KO-C(CH3)3, LAH = LIAIH4, (sia)2BH = disecondary isobutyl borane, KMNO4, HIO4 = periodic acid %3D write the missing reagents and solvents over the arrows. Some transformation require multiple steps. In some cases there will be multiple arrows. Ph -Ph Ph Ph Brarrow_forwardSpecialized reagents and their acronyms: MCPBA= meta-chloroperbenzoic acid; HOAC = acetic acid, NaOAc = Sodium Acetate; Ph= phenyl = C6H5-; P(Ph)3 = triphenyl phosphine; NBS = N- bromosuccinimide, PBR3, SOCI2, AICI3, FeBr3, H2SO4, Li, Na, Mg, Br2, CrO3, LDA = lithium diisopropylamide, PCC = pyridinium chlorochromate, KO-C(CH3)3, LAH = LIAIH4, (sia)2BH = disecondary isobutyl borane, KMNO4, HIO4 = periodic acid %3D %3D %3D %3D %3D %3D %3D write the missing reagents and solvents over the arrows. Some transformation require multiple steps. In some cases there will be multiple arrows. ОН H. (R) Br (S) HO OHarrow_forwardSpecialized reagents and their acronyms: MCPBA= meta-chloroperbenzoic acid; HOAC = acetic acid, NaOAc = Sodium Acetate; Ph= phenyl = C6H5-; P(Ph)3 = triphenyl phosphine; NBS = N- bromosuccinimide, PBr3, SOCI2, AICI3, FeBr3, H2SO4, Li, Na, Mg, Br2, CrO3, LDA = lithium diisopropylamide, PCC = pyridinium chlorochromate, KO-C(CH3)3, LAH = LIAIH4, (sia)2BH = disecondary isobutyl borane, KMNO4, HIO4 = periodic acid %3D %3D %3D %3D %3D write the missing reagents and solvents over the arrows. Some transformation require multiple steps. In some cases there will be multiple arrows. Ph CH CH o 0om ilubongo CEC-Ph In questions 14-24, write the products of the following transformations. If there is no reaction write NR. Indicate R or S or racemic or indicate cis or trans where appropriate OH + LDA THF solvent (S) Pharrow_forward
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