Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 21, Problem 20P
Interpretation Introduction
Interpretation:
In the reaction of p-chloronitrobenzene with sodium
Concept introduction:
Phenols are the compounds which bear a hydroxyl group on the benzene ring. These compounds are similar in structure to alcohols.
Sodium phenoxide is a conjugate base of phenol. It is used as precursor in the
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When 2-bromo-2-methylbutane is treated with a base, a mixture of 2-methyl-2-butene and 2-methyl-1-
butene is produced. When potassium hydroxide is the base, 2-methyl-1-butene accounts for 45% of the
product mixture. However, when potassium tert-butoxide is the base, 2-methyl-1-butene accounts for
70% of the product mixture. What percent of 2-methyl-1-butene would be in the mixture if potassium
propoxide were the base?
base
Br
A.
Less than 45%
B.
C.
45%
Between 45% and 70%
D.
More than 70%
In the following sequence of reactions which products are identified correctly?
Compound A (C 7H 11B1) is treated with magnesium in ether to give B (C 7H 11MgBr), which reacts violently with D 20 to give 1-methylcyclohexene
B with acetone (CH 3COCH 3) followed by hydrolysis gives D (C 10H 180). Heating D with
with a deuterium atom on the methyl group C. Reaction
concentrated H 2SO 4 gives E
(C 10H 16), which decolorizes two equivalents of Br 2
to give F (C 10H 16Br 2). E
undergoes hydrogenation with excess H 2 and a Pt catalyst to give isobutylcyclohexane.
O The correct structure of C is
OH
O The correct structure of D is
O The correct structure of C is
Br
OI The correct structure of F is
8r
Draw the line-angle formula of the enol formed in the following alkyne hydration reaction and then draw the
structural formula of the carbonyl compound with which this enol is in equilibrium.
-C=CH
1. (sia)2BH
2. NaOH/H₂O₂
an enol
carbonyl compound
• You do not have to consider stereochemistry.
• Draw both the enol and the carbonyl forms.
• Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom
right corner.
• Separate structures using the sign from the drop-down menu.
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Chapter 21 Solutions
Organic Chemistry
Ch. 21 - PRACTICE PROBLEM
21.1 If we examine Table 21.1, we...Ch. 21 - PRACTICE PROBLEM If we examine Table 21.1, we see...Ch. 21 - Prob. 3PPCh. 21 - PRACTICE PROBLEM
21.4 Predict the products of each...Ch. 21 - Prob. 5PPCh. 21 - PRACTICE PROBLEM
21.6 What are compounds A and B...Ch. 21 - Prob. 7PPCh. 21 - PRACTICE PROBLEM Outline a possible synthesis of...Ch. 21 - PRACTICE PROBLEM 1-Fluoro-2,4-dinitrobenzene is...Ch. 21 - PRACTICE PROBLEM
21.10 When o-chlorotoluene is...
Ch. 21 - PRACTICE PROBLEM When 2-bromo-1,3-dimethylbenzene...Ch. 21 - PRACTICE PROBLEM (a) Outline a step-by-step...Ch. 21 - Rank the following in order of increasing acidity.Ch. 21 - Prob. 14PCh. 21 - Prob. 15PCh. 21 - Describe a simple chemical test that could be used...Ch. 21 - Prob. 17PCh. 21 - Predict the product of the following reactions.Ch. 21 - 21.19 A synthesis of the β-receptor blocker called...Ch. 21 - Prob. 20PCh. 21 - When m-chlorotoluene is treated with sodium amide...Ch. 21 - Prob. 22PCh. 21 - Prob. 23PCh. 21 - Prob. 24PCh. 21 - Prob. 25PCh. 21 - Prob. 26PCh. 21 - Prob. 27PCh. 21 - Prob. 28PCh. 21 - Prob. 29PCh. 21 - Prob. 30PCh. 21 - Prob. 31PCh. 21 - 21.32 A compound X (C10H14O) dissolves in aqueous...Ch. 21 - 21.33 Compound Z (C5H10O) decolorizes bromine in...Ch. 21 - Explain why, in the case shown, the allyl group...Ch. 21 - In protic solvents the naphthoxide ion (I) is...Ch. 21 - Prob. 36PCh. 21 - Prob. 37PCh. 21 - Prob. 38PCh. 21 - Prob. 39PCh. 21 - Prob. 40PCh. 21 - 21.41 Compound W was isolated from a marine...Ch. 21 - 21.42 Phenols generally are not changed on...Ch. 21 - 21.43 Open the molecular model file for benzyne...Ch. 21 - Which of the following would be the strongest...Ch. 21 - What products would you expect from the following...Ch. 21 - Prob. 3QCh. 21 - Prob. 4QCh. 21 - 21.5 Complete the following synthesis:
Ch. 21 - Prob. 6QCh. 21 - 21.7 Select the stronger acid.
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- X Upon ozonolysis, Compound X produces two compounds: Compound Y and Compound Z. Compound Y can also be prepared from the following synthetic route: PCC 1. R₂BH, THF 1. Mg. Et₂O PCC Compound Y 2. CH₂Cl₂ 2. NaOH, HO CH₂Cl₂ 3. H₂O* From this information, draw the structures of Compounds X, Y, and Z. For Compounds X and Z, different substituents are possible. For grading purposes, just use hydrogens as the substituents. Br مرد →] ►arrow_forwardAccount for the fact that the bicyclic ether (3) is formed from the trans isomer but not from the cis isomer.arrow_forward3) Optically active alkyl bromide A (CÂH₁7Br) reactions with potassium tert-butoxide in tert- butanol to yield compound B (CH₁6). Compound B affords the carbonyl compound shown below and formaldehyde when subjected to ozonolysis followed by a reductive workup. Write the reactions and draw the structures of A & B. شدarrow_forward
- 18. Compound A (C7H₁1Br) is treated with magnesium in ether to give B (C7H11MgBr) which reacts violently with D2O to give 1-methylcyclohexene with a deuterium atom on the methyl group (C). Reaction of B with acetone followed by hydrolysis gives D (C10H180). Heating D with concentrated H2SO4 gives E (C10H16), which decolorizes two equivalents of Br2 to give F (C10H16Br4). E undergoes hydrogenation with excess of H₂ and a Pt catalyst to give isobutylcyclohexane. Determine the structures of compounds A through F by showing clearly all the reactions involved.arrow_forwardDraw the formulas of the reactants and products of the reaction: 2-ethylbutanoyl bromide with excess ethylmagnesium bromide and heating the product with concentrated H2SO4.arrow_forwardCompound A (C7H11Br) is treated with magnesium in ether to give B (C7H11MgBr), which reacts violently with D2O togive 1-methylcyclohexene with a deuterium atom on the methyl group (C). Reaction of B with acetone (CH3COCH3)followed by hydrolysis gives D (C10H18O). Heating D with concentrated H2SO4 gives E (C10H16), which decolorizestwo equivalents of Br2 to give F (C10H16Br4). E undergoes hydrogenation with excess H2 and a Pt catalyst to giveisobutylcyclohexane. Determine the structures of compounds A through F, and show your reasoning throughoutarrow_forward
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