ORGANIC CHEMISTRY-EBOOK>I<
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ISBN: 9781305084414
Author: McMurry
Publisher: INTER CENG
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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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Aldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in which there is one hydroxyl group and one ether-like group. Reaction of a hemiacetal with a second
molecule of alcohol gives an acetal and a molecule of water.
ROH, H+
OH
OR
Aldehyde/ketone
Alcohol
ROH, H+
Draw the structural formulas for the hemiacetal and the acetal formed between the following compounds:
OH
OH
OR
OR
• Use the wedge/hash bond tools to indicate stereochemistry where it exists.
+ H₂O
Which of the following tertiary alcohols cannot be prepared by the reaction of an ester with excess Grignard reagent? a. For those alcohols that can be prepared by the reaction of an ester with excess Grignard reagent, what ester and what Grignard reagent should be used?
Note: Please do not use organic reagent
Chapter 10 Solutions
ORGANIC CHEMISTRY-EBOOK>I<
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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- Aldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in which there is one hydroxyl group and one ether-like group. Reaction of a hemiacetal with a second molecule of alcohol gives an acetal and a molecule of water. We study this reaction in Chapter 16. Draw structural formulas for the hemiacetal and acetal formed from these reagents. The stoichiometry of each reaction is given in the problem.arrow_forwardPropose 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.arrow_forwardStarting with 1-pentanol identify any necessary reagents needed to make 1,2-epoxypentanearrow_forward
- Among the tertiary alcohols shown below, which one cannot be synthesized by reacting an appropriate Grignard reagent with an ester? CH2CH3 H3C-C-OH CH3 CH3 H3C-C-OH CH3 CH2CH3 H3C-C-OH CH2CH3 CH,CH3 H3C-C-OH CH(CH3)2 CH(CH3)2 H3C-C-OH CH(CH3)2arrow_forwardDetermine the structure of the methyl ester and organomagnesium bromide reagents that can be combined to form the following alcohol: Part 1: Draw the bond-line formula for the methyl ester reagent. Disregard stereochemistry. Part 2: Draw the bond-line formula for the organomagnesium bromide reagent. Disregard stereochemistry.arrow_forwardWhat are the chemical reactions for the alcohol? Choices Oxidation of primary alcoholOxidation of secondary alcoholOxidation of tertiary alcoholHydration of alkeneIntramolecular dehydrationIntermolecular dehydrationCombustionHalogenation with hydrogen halidesHalogenation with phosphorus trihalidesarrow_forward
- Give the systematic (IUPAC) names for these molecules. Boononon cnolonongron. НаСНз CHОССH2СH2СНCHЗ CH3 phenyl propanoate |4-methyl pentane methanoat Incorrect. You mixed up the acyl and alkoxy portions of the molecule. Name the alkoxy part first, followed by the acyl part.arrow_forwardWrite in the correct reagents for these transformations: a) cyclohexanol -→ chlorocyclohexane b) 2-butanone 2-butanol ward 2-butanol 2-butanone toluene - → benzoic acid nitrobenzene → anilinearrow_forward10. The Wolff-Kishner reaction, in which an aldehyde or ketone is treated with NH2NH2 and KOH, is: a) an oxidation c) an SN2 reaction b) a reduction d) a hydration 11. Which of these is most likely to dissolve in 5% NaOH? a) 1-decanol b) decanal c) decanoic acid d) 2-decanone 12. The following compound forms a cyclic hemiacetal all by itself. Draw the structure of that hemiacetal.arrow_forward
- Propose two different methods to synthesize oct-1 -en-3-ol [CH3(CH2)4CH(OH)CH = CH2] using a Grignard reagent and a carbonyl compound. Oct-1-en-3-ol is commonly called matsutake alcohol because it was rst isolated from the Japanese matsutake mushroom.arrow_forwardWhat is a good reagent to oxidize primary alcohols to aldehydes? Sodium borohydride Potassium permanganate Pyridinium chlorochromate Lithium aluminium hydride What are factors that make carbonyl groups amenable to hydrate formation Large rings, electron donating substituents Small rings, electron donating substituents Large rings, electron withdrawing substituents Small rings, electron withdrawing substituentsarrow_forwardWhen separating the two products (benzoic acid and benzyl alcohol) in the Cannizzaro reaction, you extract them between NAOH and diethyl ether. What is the compound in the aqueous layer? The sodium salt of benzoic acid Benzoic acid Benzyl alcohol O The sodium salt of benzyl alcoholarrow_forward
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