Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 21, Problem 21.64SP
A chemist was called to an abandoned aspirin factory to determine the contents of a badly corroded vat. Knowing that two salvage workers had become ill from breathing the fumes, she put on her breathing apparatus as soon as she noticed an overpowering odor like that of vinegar but much more pungent. She entered the building and took a sample of the contents of the vat. The mass spectrum showed a molecular weight of 102, and the NMR spectrum showed only a singlet at δ2.15. The IR spectrum, which appears here, left no doubt about the identity of the compound. Identify the compound, and suggest a method for its safe disposal.
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Experiment:
Each team will be provided with 5g of a mixture of acetanilide and salicylic acid. You will divide it into three 1.5 g portions in separate 125 mL Erlenmeyer flasks savıng some for melting point analysis. Dissolve the mixture in each flask in ~60mL of DI water by heating to boiling on a hotplate. Take the flasks off the hotplate once you have a clear solution and let them stand on the bench top for 5 mins and then allow them to cool as described below.
Sample A-Let the first sample cool slowly to room temperature by letting it stand on your lab bench, with occasional stirring to promote crystallization.
Sample B-Cool the second sample 1n a tap-water bath to 10-15 °C
Sample C-Cool the third sample in an ice-bath to 0-2 °C
Results:
weight after recrystalization and melting point temp.
A=0.624g,102-115°
B=0.765g, 80-105°
C=1.135g, 77-108
What is the percent yield of A,B, and C.
Chapter 21 Solutions
Organic Chemistry (9th Edition)
Ch. 21.2F - Name the following carboxylic acid derivatives,...Ch. 21.4A - Prob. 21.2PCh. 21.4A - Prob. 21.3PCh. 21.4A - Prob. 21.4PCh. 21.5C - Prob. 21.7PCh. 21.6 - When ethyl 4-hydroxybutyrate is heated in the...Ch. 21.6 - Propose a mechanism for the following ring-opening...Ch. 21.6 - Prob. 21.15PCh. 21.7B - Prob. 21.16PCh. 21.7C - Prob. 21.19P
Ch. 21.7C - Prob. 21.20PCh. 21.7C - Prob. 21.21PCh. 21.7D - Prob. 21.22PCh. 21.7D - The mechanism for acidic hydrolysis of a nitrile...Ch. 21.8A - Prob. 21.24PCh. 21.8C - Prob. 21.25PCh. 21.9 - Prob. 21.26PCh. 21.9 - Prob. 21.27PCh. 21.9 - Prob. 21.28PCh. 21.10 - Draw a mechanism for the acylation of anisole by...Ch. 21.10 - Prob. 21.30PCh. 21.11 - Prob. 21.31PCh. 21.11 - Prob. 21.32PCh. 21.12 - Problem 21-33 Propose a mechanism for the...Ch. 21.12 - Suggest the most appropriate reagent for each...Ch. 21.12 - Show how you would synthesize each compound,...Ch. 21.13 - Prob. 21.36PCh. 21.13 - Prob. 21.37PCh. 21.14 - Prob. 21.38PCh. 21.14 - Prob. 21.39PCh. 21.16 - Prob. 21.40PCh. 21.16 - Prob. 21.41PCh. 21 - Prob. 21.42SPCh. 21 - Give appropriate names for the following...Ch. 21 - Predict the major products formed when benzoyl...Ch. 21 - Predict the products of the following reactions....Ch. 21 - Prob. 21.46SPCh. 21 - Prob. 21.47SPCh. 21 - Prob. 21.48SPCh. 21 - Propose mechanisms for the following reactions.Ch. 21 - Prob. 21.51SPCh. 21 - An ether extraction of nutmeg gives large...Ch. 21 - Prob. 21.53SPCh. 21 - Show how you would accomplish the following...Ch. 21 - Prob. 21.55SPCh. 21 - Prob. 21.56SPCh. 21 - Prob. 21.57SPCh. 21 - Prob. 21.58SPCh. 21 - Prob. 21.59SPCh. 21 - Explain this curious result. What does this...Ch. 21 - Prob. 21.61SPCh. 21 - Prob. 21.62SPCh. 21 - Prob. 21.63SPCh. 21 - A chemist was called to an abandoned aspirin...Ch. 21 - Prob. 21.67SPCh. 21 - The IR spectrum, 13ONTVTR spectrum, and 1HNMR...Ch. 21 - Prob. 21.69SPCh. 21 - Prob. 21.70SPCh. 21 - Prob. 21.71SP
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