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 12.19, Problem 22P
What does a comparison of the heats of combustion of benzene (
;
]annulene (
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1,4-Pentadiene (CH2=CH-CH2-CH=CH2) is a liquid at room temperature and has a density of 0.66 g/mL and molar mass of 68.12 g/mol. In a laboratory experiment, 3.80 mL of this compound was treated with 4.80 mL of conc. H2SO4 (100% w/w; molar mass 98.08 g/mol). Note that the density of conc. H2SO4 is 1.84 g/mL. The resulting sulfate ester was then treated with 1.20 mL of water (molar mass 18.02 g/mol) affording, after work- up, 2,4-pentanediol (molar mass 104.15 g/mol) as the crude product. The crude product was then purified by simple distillation, which yielded 2.00 g of pure product.
a.
Provide a balanced chemical equation to show the reaction between 1,4-pentadiene and sulfuric acid. Do not use molecular formulas in the chemical equation except for sulfuric acid.
b.
What reactant is the limiting reagent in this chemical equation? Show calculations to support your answer.
What is the IUPAC name for the compound shown?
Step I: Identify the number of carbons in the longest chain
Step 2: Identify the base name of the molecule.
Step 3: Number the longest chain.
Step 4: Identify substituents.
Step 5: Order the substituents.
Step 6: Add the substituent locants or numbering.
Step 7: Put it all together and give the IUPAC name.
Step 4: Identify the substituents in the molecule.
A. How many methyl substituents are in the compound?
B. What prefix is needed for the methyl substituents?
C. What are the remaining substituents?
ethyl
pentyl
propyl
butyl
What is the IUPAC name for the compound shown?
Step 1: Identify the number of carbons in the longest chain
Step 2: Identify the base name of the molecule.
Step 3: Number the longest chain.
Step 4: Identify substituents.
Step 5: Order the substituents.
Step 6: Add the substituent locants or numbering.
Step 7: Put it all together and give the IUPAC name.
Step 5: Order the substituents.
Since there are multiple substituents present, we must next consider the order the substituents in the name.
The substituent order should be
methyl, ethyl, followed by propyl
ethyl, propyl, followed by trimethyl
trimethyl, ethyl followed by propyl
O ethyl, trimethyl, followed by propyl
Chapter 12 Solutions
Organic Chemistry - Standalone book
Ch. 12.2 - Write structural formulas for toluene (C6H5CH3)...Ch. 12.3 - Prob. 2PCh. 12.5 - Prob. 3PCh. 12.5 - Prob. 4PCh. 12.6 - Prob. 5PCh. 12.6 - Chrysene is an aromatic hydrocarbon found in coal...Ch. 12.8 - Prob. 7PCh. 12.9 - As measured by their first-order rate constants,...Ch. 12.9 - Give the structure of the principal organic...Ch. 12.9 - Prob. 10P
Ch. 12.10 - Prob. 11PCh. 12.11 - Prob. 12PCh. 12.12 - Prob. 13PCh. 12.13 - Prob. 14PCh. 12.13 - Prob. 15PCh. 12.15 - The regioselectivity of Birch reduction of...Ch. 12.16 - Prob. 17PCh. 12.17 - Both cyclooctatetraene and styrene have the...Ch. 12.17 - Prob. 19PCh. 12.18 - Give an explanation for each of the following...Ch. 12.19 - Prob. 21PCh. 12.19 - What does a comparison of the heats of combustion...Ch. 12.20 - Prob. 23PCh. 12.20 - Prob. 24PCh. 12.20 - Prob. 25PCh. 12.20 - Prob. 26PCh. 12.20 - Prob. 27PCh. 12.20 - Prob. 28PCh. 12.21 - Prob. 29PCh. 12.21 - Prob. 30PCh. 12.22 - Prob. 31PCh. 12.22 - Prob. 32PCh. 12 - Write structural formulas and give the IUPAC names...Ch. 12 - Prob. 34PCh. 12 - Prob. 35PCh. 12 - Prob. 36PCh. 12 - Prob. 37PCh. 12 - Acridine is a heterocyclic aromatic compound...Ch. 12 - Prob. 39PCh. 12 - Prob. 40PCh. 12 - Prob. 41PCh. 12 - Evaluate each of the following processes applied...Ch. 12 - Prob. 43PCh. 12 - Prob. 44PCh. 12 - Prob. 45PCh. 12 - Prob. 46PCh. 12 - Anthracene undergoes a DielsAlder reaction with...Ch. 12 - Prob. 48PCh. 12 - Prob. 49PCh. 12 - The relative rates of reaction of ethane, toluene,...Ch. 12 - Both 1,2-dihydronaphthalene and...Ch. 12 - Prob. 52PCh. 12 - Prob. 53PCh. 12 - Prob. 54PCh. 12 - Prob. 55PCh. 12 - Prob. 56PCh. 12 - Each of the following reactions has been described...Ch. 12 - Prob. 58PCh. 12 - A compound was obtained from a natural product and...Ch. 12 - Prob. 60PCh. 12 - Suggest reagents suitable for carrying out each of...Ch. 12 - Prob. 62PCh. 12 - Prob. 63DSPCh. 12 - Prob. 64DSPCh. 12 - Prob. 65DSPCh. 12 - Prob. 66DSP
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- What is the IUPAC name for the compound shown? Step 1: Identify the number of carbons in the longest chain Step 2: Identify the base name of the molecule. Step 3: Number the longest chain. Step 4: Identify substituents. Step 5: Order the substituents. Step 6: Add the substituent locants or numbering. Step 7: Put it all together and give the IUPAC name. Step 7: Put it all together and give the IUPAC name. You have determined the name of the longest carbon chain and the locations and name of the substituents. Complete the name of the molecule by adding in the hyphens and commas. 3ethyl223trimethyl5propyldecane JUPAC name:arrow_forwardif the heat of hydrogenation for cyclohexene is 120 kj mol and 1,3 cyclohexane is less than 240 kj mol, what is the heat of hydrogenation for benzene? thank you ^___^arrow_forwardWhat is the IUPAC name for the compound shown? Step 1: Identify the number of carbons in the longest chain Step 2: Identify the base name of the molecule. Step 3: Number the longest chain. Step 4: Identify substituents. Step 5: Order the substituents. Step 6: Add the substituent locants or numbering. Step 7: Put it all together and give the IUPAC name. Step 6: Add the substituent locants or numbering. Now that you have identified the order of the substituents, you need to provide the locant, which indicates the number carbon on the main chain where each substituent is placed. Carbon 5 has only one substituent, so the name is represented by 5-propyl. Both carbons 2 and 3 have two substituents. What would be the correct naming for those carbons? The substituents should be named: 2,2-dimethyl and 3-methyl-3-ethyl 2,3-trimethyl and 3-ethyl 2,2,3-trimethyl and 3-ethyl 2-dimethyl and 3-methylethylarrow_forward
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