Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 10.SE, Problem 42AP
Why do you suppose it’s not possible to prepare a Grignard reagent from a bromo alcohol such as 4-bromo-1-pentanol? Give another example of a molecule that is unlikely to form a Grignard reagent.
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Propose two different methods to synthesize 1-octen-3-ol [CH3(CH2),CH(OH)CH=CH] using a Grignard reagent and a carbonyl
compound. 1-Octen-3-ol is commonly called matsutake alcohol because it was first isolated from the Japanese matsutake
mushroom.
Esterification reactions, such as the one below, is a poor synthetic strategy as it leads to poor yields of the ester. What alternative could be done to produce more p-methylphenyl acetate?
Replace the aromatic alcohol with a phenolate.
Replace acetic acid with acetate.
Replace the p-methylphenol with p-chlorotoluene.
Replace acetic acid with acetyl chloride.
Why must dehydration reactions of alcohols be carried out under acid catalysis?
O 1) the hydroxide group is a poor leaving group and must be protonated to
1)
generate a better leaving group.
2) the hydroxide group is a great leaving group and does not need to be
protonated to generate a better leaving group.
O 3) the acid isn't necessary for the reaction.
O4)
None of these are correct answers.
Chapter 10 Solutions
Organic Chemistry
Ch. 10.1 - Prob. 1PCh. 10.1 - Draw structures corresponding to the following...Ch. 10.2 - Prob. 3PCh. 10.2 - Taking the relative reactivities of 1°, 2°, and...Ch. 10.4 - Prob. 5PCh. 10.4 - The major product of the reaction of...Ch. 10.4 - Prob. 7PCh. 10.5 - Prob. 8PCh. 10.6 - Prob. 9PCh. 10.6 - How might you replace a halogen substituent by a...
Ch. 10.7 - How would you carry out the following...Ch. 10.8 - Rank both sets of compounds in order of increasing...Ch. 10.8 - Tell whether each of the following reactions is an...Ch. 10.SE - Prob. 14VCCh. 10.SE - Prob. 15VCCh. 10.SE - Prob. 16VCCh. 10.SE - Draw the electron-pushing mechanism for each...Ch. 10.SE - Draw the electron-pushing mechanism for the...Ch. 10.SE - The formation of Br2 from NBS first involves the...Ch. 10.SE - In light of the fact that tertiary alkyl halides...Ch. 10.SE - Alkyl halides can be reduced to alkanes by a...Ch. 10.SE - Name the following alkyl halides:Ch. 10.SE - Prob. 23APCh. 10.SE - Draw and name all of the monochlorination products...Ch. 10.SE - How would you prepare the following compounds,...Ch. 10.SE - Prob. 26APCh. 10.SE - A chemist requires a large amount of...Ch. 10.SE - What product(s) would you expect from the reaction...Ch. 10.SE - What product(s) would you expect from the reaction...Ch. 10.SE - What product would you expect from the reaction of...Ch. 10.SE - Rank the compounds in each of the following series...Ch. 10.SE - Which of the following compounds have the same...Ch. 10.SE - Tell whether each of the following reactions is an...Ch. 10.SE - Prob. 34APCh. 10.SE - Alkylbenzenes such as toluene (methylbenzene)...Ch. 10.SE - Prob. 36APCh. 10.SE - Prob. 37APCh. 10.SE - Prob. 38APCh. 10.SE - Prob. 39APCh. 10.SE - Prob. 40APCh. 10.SE - The syntheses shown here are unlikely to occur as...Ch. 10.SE - Why do you suppose its not possible to prepare a...Ch. 10.SE - Prob. 43APCh. 10.SE - Identify the reagents a–c in the following...Ch. 10.SE - Prob. 45APCh. 10.SE - Prob. 46APCh. 10.SE - Prob. 47APCh. 10.SE - The relative rate of radical bromination is...Ch. 10.SE - Prob. 49APCh. 10.SE - Predict the product and provide the entire...
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- Using your reaction roadmap as a guide, show how to convert ethylene into 1-butene. All of the carbon atoms of the target molecule must be derived from ethylene. Show all intermediate molecules synthesized along the way. Ethylene 1-Butenearrow_forwardHow would you use a Grignard reaction of an aldehyde or ketone to synthesize 3-pentanol? Draw the Grignard reagent and the aldehyde or ketone you would use below. • 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. • Draw the Grignard reagent as a covalent magnesium bromide. • In cases where there is more than one answer, just give one. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate multiple reactants using the + sign from the drop-down menu. ?arrow_forwardNitesharrow_forward
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