Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 11.1, Problem 1P
The aromas of many flowers and fruits are due to esters such as those shown in this problem. What are the common names of these esters? (Also see Problem 41.)
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Hydration of aldehydes and ketones can be catalyzed by acid
or base. Bases catalyze hydration by:
protonating the carbonyl oxygen
making the carbonyl group more electrophilic
employing hydroxide ion, which is a better nucleophile than water
making the carbonyl group less electrophilic
shifting the equilibrium position of the reaction to favor products
What explains why many aldehydes and ketones can undergo self- condensation reactions in basic conditions?
The alpha carbon can lose a proton and act like a nucleophile and the carbonyl carbon a an electrophile
O The alpha carbon can gain a proton and act like an electrophile and the carbonyl carbon is a nucleophile
O The oxygen of the carbonyl group can attack the carbon of the carbonyl group
Only esters can undergo self-condensation reactions
4.
Aldehydes and ketones can be "protected" as acetals and ketals. Complete the following outlined
reactions, showing how the protection is accomplished, and what results after deprotection.
Br
MgBr
1)
Br
2) H3O*
deprotection here
Chapter 11 Solutions
Essential Organic Chemistry (3rd Edition)
Ch. 11.1 - The aromas of many flowers and fruits are due to...Ch. 11.1 - Name the following compounds:Ch. 11.1 - Prob. 3PCh. 11.2 - Prob. 4PCh. 11.2 - Prob. 5PCh. 11.4 - a. What is the product of the reaction of acetyl...Ch. 11.4 - Prob. 7PCh. 11.5 - Using the pKa values listed in Table 11.1, predict...Ch. 11.6 - Starting with acetyl chloride, what neutral...Ch. 11.6 - Prob. 10P
Ch. 11.7 - Prob. 11PCh. 11.8 - Prob. 13PCh. 11.8 - Using the mechanism for the acidcatalyzed...Ch. 11.8 - Prob. 15PCh. 11.8 - Prob. 16PCh. 11.8 - Prob. 17PCh. 11.9 - Prob. 18PCh. 11.10 - Show how each of the following esters could be...Ch. 11.11 - Which of the following reactions would lead to the...Ch. 11.12 - Prob. 22PCh. 11.12 - Prob. 23PCh. 11.13 - Prob. 24PCh. 11.13 - Prob. 25PCh. 11.14 - Prob. 26PCh. 11.14 - Prob. 27PCh. 11.14 - Prob. 28PCh. 11.15 - Prob. 29PCh. 11.15 - How would you synthesize the following compounds...Ch. 11 - Write a structure for each of the following a. N,N...Ch. 11 - Prob. 32PCh. 11 - Which ester is more reactive, methyl acetate or...Ch. 11 - What products would be formed from the reaction of...Ch. 11 - What products would be obtained from the following...Ch. 11 - Prob. 36PCh. 11 - a. Which compound would you expect to have a...Ch. 11 - a. List the following esters in order of...Ch. 11 - D. N. Kursanov, a Russian chemist, proved that the...Ch. 11 - Prob. 40PCh. 11 - Using an alcohol for one method and an alkyl...Ch. 11 - Prob. 42PCh. 11 - Prob. 44PCh. 11 - Prob. 45PCh. 11 - Prob. 46PCh. 11 - Prob. 47PCh. 11 - Prob. 48PCh. 11 - Prob. 49PCh. 11 - Show how the following compounds could be prepared...Ch. 11 - Prob. 51PCh. 11 - Prob. 52PCh. 11 - Prob. 53P
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- The major product that will form during the nitration of benzoic acid is? OA H₂N OR O-N ос OD. NO₂ COOH COOH COOR NH₂ COOH OZN H-N COOH COOHarrow_forwardWhich of these would likely take the LONGEST to hydrolyze (undergo hydralysis) to the carboxylic acid? 人 人 OH A. D. O All would hydrolyze rapidly B would be slowest O C would be slowest O D would be slowestarrow_forwardFollowing ester (methyl benzoate) was hydrolyzed in presence of an acid catalyst. This reaction produces --- and ---. OCH3 benzoic acid, ethanol benzoic acid, water acetic acid, benzene benzoic acid, methanolarrow_forward
- Complete the following reactions by filling in any missing reactants, reagents or products. a) Zn(Hg) conc. HCl b) ОН ? с) ОН РСС CH,Cl,arrow_forwardWhat explains why many aldehydes and ketones can undergo self-condensation reactions in basic conditions? The alpha carbon can lose a proton and act like a nucleophile and the carbonyl carbon is an electrophile. The alpha carbon can gain a proton and act like an electrophile and the carbonyl carbon is a nucleophile. The oxygen of the carbonyl group can attack the carbon of the carbonyl group. Only esters can undergo self-condensation reactions.arrow_forwardA mixture of the compounds shown below is dissolved in cyclohexane. An aqueous solution of NaOH is added to the solution, and two layers are formed. Which compound(s) is(are) found in the aqueous layer? он HO Benzoic acid Beta-naphthol Naphthalene O Benzoic acid only O Beta-naphthol only O Naphthalene O Both Benzoic acid and beta-naphthol O Both beta-naphthol and naphthalenearrow_forward
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