Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 13.3, Problem 3P
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Draw the line-angle formula of the enol formed in the following alkyne hydration reaction and then draw the
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-C=CH
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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
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• Separate structures using the sign from the drop-down menu.
ChemDoodleⓇ
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Fill in the table with the partial charges of the atoms. The atoms are numbered with
the following scheme with respect to the substituent on the aromatic ring.
x c/
3.
|
H./
Atom
Chlorobenzene
Nitrobenzene
Aminobenzene
C2
Ca
Which substituent results in a ring atom with the greatest positive charge (smallest
negative charges)?
What is the mechanism that causes this pattern of electron distribution on the
aromatic ring? Diagram the mechanism.
Which substituent results in a ring atom with the least positive charge (largest
negative charges)?
What is the mechanism that causes this pattern of electron distribution on the
aromatic ring? Diagram the mechanism.
3A. During the workup portion of the reaction of alkenes with
HBr as described in the experiment provided, a student transferred
the reaction mixture to a separatory funnel, rinsed the reaction
flask with diethyl ether, and added the ether rinses to the
separatory funnel. The student then added sodium bicarbonate to
the separatory funnel. Extremely vigorous bubbling occurred.
What did the student do wrong? Can they still isolate the
product? If so describe the next steps the student should take to
isolate the product.
Chapter 13 Solutions
Organic Chemistry - Standalone book
Ch. 13.2 - Based on Hammonds postulate which holds that the...Ch. 13.3 - Prob. 2PCh. 13.3 - Using : O =N+= O : as the electrophile, write a...Ch. 13.4 - Prob. 4PCh. 13.5 - Prob. 5PCh. 13.6 - Prob. 6PCh. 13.6 - Write a reasonable mechanism for the formation of...Ch. 13.6 - tert-Butylbenzene can be prepared by alkylation of...Ch. 13.6 - Prob. 9PCh. 13.7 - The reaction shown gives a single product in 88...
Ch. 13.7 - Prob. 11PCh. 13.8 - Using benzene and any necessary organic or...Ch. 13.10 - Prob. 13PCh. 13.11 - Prob. 14PCh. 13.12 - Prob. 15PCh. 13.12 - Prob. 16PCh. 13.13 - Prob. 17PCh. 13.13 - Prob. 18PCh. 13.14 - Reaction of chlorobenzene with p-chlorobenzyl...Ch. 13.15 - Prob. 20PCh. 13.15 - Prob. 21PCh. 13.15 - Prob. 22PCh. 13.16 - Prob. 23PCh. 13.16 - Prob. 24PCh. 13.17 - Prob. 25PCh. 13.18 - Prob. 26PCh. 13.19 - Write the structure of the expected product from...Ch. 13.20 - Prob. 28PCh. 13.20 - Prob. 29PCh. 13.21 - Prob. 30PCh. 13.21 - Offer an explanation for the observation that...Ch. 13.21 - Prob. 32PCh. 13 - Write the structure of the organic product in each...Ch. 13 - Prob. 34PCh. 13 - Prob. 35PCh. 13 - Prob. 36PCh. 13 - Prob. 37PCh. 13 - Prob. 38PCh. 13 - Prob. 39PCh. 13 - Treatment of the alcohol shown with sulphuric acid...Ch. 13 - Prob. 41PCh. 13 - Prob. 42PCh. 13 - Prob. 43PCh. 13 - Arrange the following five compounds in order of...Ch. 13 - Prob. 45PCh. 13 - Prob. 46PCh. 13 - Prob. 47PCh. 13 - Give reagents suitable for carrying out each of...Ch. 13 - Prob. 49PCh. 13 - Prob. 50PCh. 13 - Which is the best synthesis of the compound shown?Ch. 13 - What combination of acyl chloride or acid...Ch. 13 - A standard synthetic sequence for building a...Ch. 13 - Prob. 54PCh. 13 - Prob. 55PCh. 13 - Prob. 56PCh. 13 - Prob. 57PCh. 13 - Prob. 58PCh. 13 - Prob. 59PCh. 13 - Prob. 60DSPCh. 13 - Prob. 61DSPCh. 13 - Prob. 62DSPCh. 13 - Prob. 63DSP
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- Draw the product of the reaction shown below. Use dash and/or wedge bonds to indicate stereochemistry where appropriate. Ignore inorganic byproducts. OH 11110 PC|3 pyridine Qarrow_forwardEthers can be prepared by reaction of an alkoxide or phenoxide ion with a primary alkyl halide. Draw the structure of the expected organic product of the reaction of iodomethane with the following alkoxide ion: CH3 H3C O Na You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • Do not include counter-ions, e.g., Na", I, in your answer. орy вste ChemDoodlearrow_forwardEthers can be prepared by reaction of an alkoxide or phenoxide ion with a primary alkyl halide. Draw the structure of the expected organic product of the reaction of 1-iodo-2-methylpropane with the following alkoxide ic + O Na You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • Do not include counter-ions, e.g., Na", I", in your answer. C opy astearrow_forward
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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%arrow_forwardWrite an equation for the acid-base reaction between 2,4-pentanedione and sodium eth- oxide and calculate its equilibrium constant, K. The pK, of 2,4-pentanedione is 9; that of ethanol is 15.9. CH,CCHÖCH, + CH,CH,O Na* H 2,4-Pentanedione Sodium ethoxidearrow_forwardChemistry 3. The following sequence generates crystals. The crystals produced are insoluble in organic solvents but freely soluble in water. They have a melting point of 203 °C. There is an instantaneous precipitate formed with silver nitrate solution. Catalytic hydrogenation gives cycloheptane. What is the crystalline compound? Why does it have these unexpected properties? heat 1 equiv Br2 dibromide crystals - HBr tropilidenearrow_forward
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