Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Textbook Question
Chapter 16.7, Problem 15P
What is the product of an acyl substitution reaction—a new
- a. a stronger base than the substituent that is attached to the acyl group
- b. a weaker base than the substituent that is attached to the acyl group
- c. similar in basicity to the substituent that is attached to the acyl group
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What explains why many aldehydes and ketones can undergo self- condensation reactions in basic conditions?
A. The alpha carbon can lose a proton and act like a nucleophile and the carbonyl carbon a an electrophile
B. The alpha carbon can gain a proton and act like an electrophile and the carbonyl carbon is a nucleophile
C. The oxygen of the carbonyl group can attack the carbon of the carbonyl group
D. Only esters can undergo self-condensation reactions
Reactions of carbonyl compounds with hydride ion donors.
a. Draw reaction of an aldehyde with sodium borohydride forms a primary alcohol.
b. Draw reaction of a ketone with sodium borohydride forms a secondary alcohol.
What is the major difference between the base-catalyzed and acid-catalyzed processes for nucleophilic addition of water to aldehydes and ketones?
a. The base-catalyzed reaction takes place rapidly because hydroxide ion is a much better nucleophile than neutral water.
b. The rate of reaction in base catalyzed process is slower than acid catalyzed process.
c. The acid-catalyzed reaction takes place rapidly because the protonated carbonyl compound is a much better electrophile than the neutral compound.
d. Only 1 and 3 are correct.
Chapter 16 Solutions
Organic Chemistry
Ch. 16.1 - The aromas of many flowers and fruits are due to...Ch. 16.1 - Prob. 2PCh. 16.1 - Name the following:Ch. 16.1 - Prob. 4PCh. 16.2 - Prob. 5PCh. 16.2 - Which is longer, the carbon-oxygen single bond in...Ch. 16.2 - There are three carbon-oxygen bonds in methyl...Ch. 16.2 - Prob. 8PCh. 16.4 - Prob. 9PCh. 16.4 - Prob. 10P
Ch. 16.5 - a. What is the product of the reaction of acetyl...Ch. 16.6 - a. Which compound has the stretching vibration for...Ch. 16.6 - Using the pKa values listed in Table 15.1, predict...Ch. 16.6 - Is the following statement true or false? If the...Ch. 16.7 - What is the product of an acyl substitution...Ch. 16.8 - PROBLEM 16
Starting with acetyl chloride, what...Ch. 16.8 - Prob. 18PCh. 16.9 - We saw that it is necessary to use excess amine in...Ch. 16.9 - Prob. 20PCh. 16.9 - a. state three factors that cause the uncatalyzed...Ch. 16.10 - Prob. 23PCh. 16.10 - Using the mechanism for the acid-catalyzed...Ch. 16.10 - Prob. 25PCh. 16.10 - Prob. 27PCh. 16.10 - Write the mechanism for the acid-catalyzed...Ch. 16.10 - Write the mechanism for the acid-catalyzed...Ch. 16.11 - Prob. 30PCh. 16.12 - Prob. 31PCh. 16.12 - Prob. 32PCh. 16.13 - Prob. 34PCh. 16.13 - Which has a higher melting point, glyceryl...Ch. 16.13 - Draw the structure of an optically inactive fat...Ch. 16.13 - Draw the structure of an optically active fat...Ch. 16.14 - Show how each of the following esters could he...Ch. 16.14 - Prob. 39PCh. 16.15 - Prob. 40PCh. 16.15 - Which of the following reactions leads to the...Ch. 16.16 - Prob. 42PCh. 16.16 - Prob. 43PCh. 16.18 - Prob. 44PCh. 16.18 - Prob. 45PCh. 16.19 - Prob. 46PCh. 16.19 - Which alkyl halides from the carboxylic acids...Ch. 16.20 - Prob. 49PCh. 16.20 - Prob. 50PCh. 16.20 - Prob. 51PCh. 16.21 - Prob. 52PCh. 16.21 - Prob. 53PCh. 16.22 - How could you synthesize the following compounds...Ch. 16 - Prob. 55PCh. 16 - Name the following:Ch. 16 - Prob. 57PCh. 16 - What compound are obtained from the fallowing...Ch. 16 - a. Rank the following esters in order of...Ch. 16 - Because bromocyclohexane is a secondary alkyl...Ch. 16 - a. Which compound would you expect to have a...Ch. 16 - How could you use 1H NMR spectroscopy to...Ch. 16 - Prob. 63PCh. 16 - a. When a carboxylic acid is dissolved in...Ch. 16 - Rank the following compounds in order of...Ch. 16 - Prob. 66PCh. 16 - Prob. 67PCh. 16 - Prob. 68PCh. 16 - A compound with molecular formula C5H10O2 gives...Ch. 16 - Prob. 70PCh. 16 - Prob. 71PCh. 16 - Prob. 72PCh. 16 - Two products, A and B, are obtained from the...Ch. 16 - Prob. 74PCh. 16 - Prob. 75PCh. 16 - Prob. 76PCh. 16 - Prob. 77PCh. 16 - When treated with an equivalent of methanol,...Ch. 16 - a. Identify the two products obtained from the...Ch. 16 - Prob. 80PCh. 16 - Identity the major and minor products of the...Ch. 16 - Prob. 82PCh. 16 - When a compound with molecular formula C11H14O2...Ch. 16 - Prob. 84PCh. 16 - Prob. 85PCh. 16 - The 1H NMR spectra for two esters with molecular...Ch. 16 - Show how the following compounds could be prepared...Ch. 16 - Prob. 88PCh. 16 - Prob. 89PCh. 16 - Prob. 90PCh. 16 - The intermediate shown here is formed during the...Ch. 16 - Prob. 92PCh. 16 - Propose a mechanism that accounts for the...Ch. 16 - Catalytic antibodies catalyze a reaction by...Ch. 16 - Prob. 95P
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- 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 reactionsarrow_forwardConsider the structure of pent-2-ene, if it undergoes ozonolysis, which of the following final product is formed? a.Ethanal and Propanal b.Ethanal and Propanone c.CO2 and Propanal d.Ethanal and CO2arrow_forwardTo prepare an ether from an alkyl halide by a nucleophilic substitution reaction, what are the two types of nucleophiles that can be used?arrow_forward
- 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 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_forwardGrignard reagent is a nucleophile. Which electrons does it give up in the reaction? a) Electrons in the bond between carbon and chlorine b) Bond electrons between carbon and magnesium c) An electron pair from the p-electrons of the aromatic ring d) Electrons in the bond between magnesium and chlorinearrow_forwarde) sec-butyl bromide • Question 2: Identify the nucleophile and leaving group and draw the products of each reaction. a. b. Br + + OCH₂CH3 NaOH d. Br + N3 + NaCNarrow_forward
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