Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Textbook Question
Chapter 19, Problem 69P
Show how the following compounds can be synthesized from benzene:
a. N,N,N-trimethylanilinium iodide
b. 2-methy 1-4-nitrophcnol
c. p-benzylchlorobenzene
d. benzyl methyl ether
e. p-nitroaruline
f. m-bromoiodobenzene
g. p-dideuteriobenzene
h. p-nitro-N-methylaniline
i. 1-bromo-3-nitrobenzene
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Students have asked these similar questions
Propose syntheses of the following compounds starting with benzene or toluene. Assume ortho and
isomers can be separated.
a.
b.
O₂N-
Cl
COOH
para
0. Propose syntheses to carry out each of the following conversions. Assume ortho and para isomers can
be separated
a.
Br
b.
COOH
CH3
NH₂
PABA
(active ingredient in some sunscreens)
H3C
H
C=C
CH3
H
m-chloroperoxybenzoic acid
CH2Cl2, rt
C-C--.
H3CH2CC
H
H3C CH3
Cl₂
H₂O
NaOH
H₂O
D.
S-
E.
CH3
H₂O₂, H₂O
It
CH₂O Na
+
CHI
F.
HI, H₂O
heat
G.
4
OH
CH3CHCH3 + ICH2CH3
1. NaH
(CH3)3COH
(CH3)3 COCHCH2CH3
2.
CH3
5. Show how the ether below could be prepared from toluene and any other necessary reagents. Show all
reagents and all intermediate structures.
H3C-
H3C-
CI
OCH2CH3
Chapter 19 Solutions
Organic Chemistry
Ch. 19.1 - Draw the structure for each of the following: a....Ch. 19.2 - PROBLEM 2
If electrophilic addition to benzene is...Ch. 19.4 - Why does hydration inactivate FeBr3?Ch. 19.6 - Prob. 5PCh. 19.7 - Prob. 6PCh. 19.8 - What is the major product of a Friedel-Crafts...Ch. 19.10 - Describe two ways to prepare each of the following...Ch. 19.12 - Prob. 9PCh. 19.13 - Name the following:Ch. 19.13 - Prob. 12P
Ch. 19.13 - Prob. 13PCh. 19.13 - Prob. 14PCh. 19.14 - Prob. 15PCh. 19.14 - List the compounds in each set from most reactive...Ch. 19.15 - Prob. 18PCh. 19.15 - What product(s) result from nitration of each of...Ch. 19.15 - Prob. 20PCh. 19.16 - Which acid in each of the following pairs is...Ch. 19.16 - Prob. 23PCh. 19.16 - Prob. 24PCh. 19.18 - Show how the following compounds can be...Ch. 19.18 - Give the products, if any, of each of the...Ch. 19.19 - a. Does a coupling reaction have to be used to...Ch. 19.19 - PROBLEM 28
Show how each of the following...Ch. 19.20 - What is the major product(s) of each of the...Ch. 19.20 - Prob. 30PCh. 19.21 - Why isn't FeBr3 used as a catalyst in the first...Ch. 19.21 - Prob. 33PCh. 19.21 - Write the sequence of steps required for the...Ch. 19.21 - Prob. 35PCh. 19.22 - What product is formed from reaction of...Ch. 19.22 - Prob. 37PCh. 19.22 - Draw the structure of the activated ring and the...Ch. 19.23 - Prob. 39PCh. 19.23 - Prob. 40PCh. 19.23 - Diazomethane can be used to convert a carboxylic...Ch. 19.24 - Prob. 42PCh. 19.24 - Prob. 43PCh. 19.24 - Prob. 44PCh. 19.25 - Prob. 45PCh. 19 - Draw the structure for each of the following: a....Ch. 19 - Prob. 47PCh. 19 - Prob. 48PCh. 19 - Prob. 49PCh. 19 - For each of the statements in Column I, choose a...Ch. 19 - What product is obtained from the reaction of...Ch. 19 - Draw the product(s) of each of the following...Ch. 19 - Rank the following substituted anilines from most...Ch. 19 - Prob. 54PCh. 19 - The compound with the 1H NMR spectrum shown below...Ch. 19 - Prob. 56PCh. 19 - Show how the following compounds can be...Ch. 19 - Prob. 58PCh. 19 - Rank each group of compounds from most reactive to...Ch. 19 - Prob. 60PCh. 19 - Describe two ways to prepare anisole from benzene.Ch. 19 - For each of the following components, indicate the...Ch. 19 - Prob. 63PCh. 19 - Prob. 64PCh. 19 - Prob. 65PCh. 19 - Prob. 66PCh. 19 - An aromatic hydrocarbon with a molecular formula...Ch. 19 - The following tertiary alkyl bromides undergo an...Ch. 19 - Show how the following compounds can be...Ch. 19 - Use the four compounds shown below to answer the...Ch. 19 - a. Rank the following esters from most reactive to...Ch. 19 - A mixture of 0.10 mol benzene and 0.10 mol...Ch. 19 - Prob. 73PCh. 19 - Benzene underwent a Friedel-Crafts acylation...Ch. 19 - Prob. 75PCh. 19 - Prob. 76PCh. 19 - Prob. 77PCh. 19 - Friedel-Crafts alkylations can be carried out with...Ch. 19 - Show how the following compounds can be prepared...Ch. 19 - Prob. 80PCh. 19 - Prob. 81PCh. 19 - a. Describe four ways the following reaction can...Ch. 19 - Propose a mechanism for each of the following...Ch. 19 - Prob. 84PCh. 19 - Describe how naphthalene can he prepared from the...Ch. 19 - Prob. 86PCh. 19 - Using resonance contributors for the carbocation...Ch. 19 - Prob. 88PCh. 19 - When heated with chromic acid, compound A forms...Ch. 19 - Prob. 90PCh. 19 - Prob. 91PCh. 19 - What reagents are required to carry out the...Ch. 19 - Show how the following compounds can be prepared...Ch. 19 - An unknown compound reacts with ethyl chloride and...Ch. 19 - How can you distinguish the following compounds...Ch. 19 - P-Fluoronitrobenzene is more reactive toward...Ch. 19 - a. Explain why the following reaction leads to the...Ch. 19 - Describe how mescaline can be synthesized from...Ch. 19 - Propose a mechanism for the following reaction...Ch. 19 - Explain why hydroxide ion catalyzes the reaction...Ch. 19 - Propose a mechanism for each of the following...Ch. 19 - Prob. 102PCh. 19 - Prob. 103PCh. 19 - Describe how 3-methyl-1-phenyl-3-pentanol can he...Ch. 19 - a. How can aspirin be synthesized from benzene? b....Ch. 19 - Prob. 106PCh. 19 - Show how Novocain, a painkiller used frequently by...Ch. 19 - Prob. 108PCh. 19 - Saccharin, an artificial sweetener, is about 300...
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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
- Given the major organic product(s) of each of the following reactions. If none is predicted, write "N.R." [answer 61 a. b. H3C C. NO₂ CH3CH2CH2Cl AICI 3 1) NaOH CI 2) H3O+ NO₂ 1. SnCl2, H3O+ 2. NaOH 3arrow_forwardPlease correct answer and don't used hand raitingarrow_forwardTo answer the following questions, consider the reaction below: CH3 . CH3 OH a. The best reagents for accomplishing the above transformation are.... a. 1. OsO4, pyridine 2. NaHSO3, H₂O b. 1. Hg(OAc)2, H₂O 1. C. 2. NaBH4 RCO₂H, CH2Cl₂ 2. H₂O* d. 1. BH3, THF 2. H₂O₂, OH b. The alcohol product is classified as a: a. 1° alcohol b. 2° alcohol C. 3° alcohol d. 4° alcohol c. The conversion of an alcohol into an alkyl chloride by reaction with SOCI2 is an example of: a. b. ن نخنه C. d. an El process an Syl process an E2 process an Sy2 processarrow_forward
- Estimation of ash in food Questions: Q1: What does the word ash refer to? Q2: Mention the types of ash in food Q3: Mention the benefit of using a glass dryerarrow_forwardDraw structures corresponding to the names given a. m-fluoronitrobenzene b. p-bromoaniline c. o-chlorophenol d. 3,5-dimethylbenzoic acidarrow_forwardIllustrate the reaction mechanism the following reactionarrow_forward
- Propose a synthesis for the following compound using benzene or toluene and any other reagents necessary. Show all major intermediate compounds that would probably be isolated during the course of your synthesis. on. Harrow_forwardProvide correct IUPAC names for each of the following compounds. NOT a. b. C. 2003 H,N- CH3 NH2 CHarrow_forward. Consider the reaction below to answer the following questions. OH 1. NaH 2. CH3I, ether O-CH3 A. Write the complete stepwise mechanism for the reaction. Show all intermediate structures and all electron flow with arrows. B. Mechanistically, the Williamson ether synthesis outlined above is: ن نخنه a. an El process b. an SN1 process C. an E2 process d. an SN2 process C. Alternatively, cyclopentyl methyl ether may be synthesized from cyclopentene. synthesis of cyclopentyl methyl ether from cyclopentene. Outline aarrow_forward
- Q2. A good synthesis of (CH3)3C- would be: A) B) CSI3 0 CH3CC1 (CH3) 3CC1 Benzene AlCl3 AlCl3 (CH3)3CC1 CH3CC1 Benzene C) AlCl3 0 AlCl3 CH3CC1 (CH3) 2C-CH2 Bonzone AlCl3 HF D) More than one of these E) None of thesearrow_forwardDon't used hand raiting and correct answer and don't used Ai solutionarrow_forwardShow how you might carry out the following transformation or reactions: toluene to m-chlorobenzoic acidarrow_forward
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