MASTERING ORGANIC CHEMISTRY W/ETEXT >I
14th Edition
ISBN: 9781269926454
Author: Pearson
Publisher: PEARSON C
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 16.7, Problem 15P
What is the product of an acyl substitution reaction—a new carboxylic acid derivative, a mixture of two carboxylic acid derivatives, or no reaction—if the new group in the tetrahedral intermediate is the following?
- 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
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
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
What is the importance of proton transfer in the formation of ester?
A.The carbonyl carbon is easily attacked by the nucleophile.
B. The oxygen that has been attached to the two alkyl groups will become stable.
C. The removal of a bulky substituent attached to the reactive site stabilizes the compound.
D. none of the above
In Chapter 18, we will learn about the hydrolysis of acetals to aldehydes and ketones. Four of the seven steps in the mechanism for this process are shown in the conversion of acetal A to hemiacetal E.
a.Add curved arrows for each step.
b.Draw another resonance structure for C.
c.Identify the nucleophile and electrophile in Step [3].
d.Which steps are Brønsted–Lowry acid–base reactions?
Chapter 16 Solutions
MASTERING ORGANIC CHEMISTRY W/ETEXT >I
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
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- When toluene is treated with sulfuric and nitric acids under special conditions, three nitro (NO2) groups are substituted for hydrogens at the 2, 4 and 6 positions on the ring (the next section discusses why the 2, 4, and 6 positions are substituted). The product is a highly explosive substance called 2,4,6-trinitrotoluene. This subastance is commonly known by a three letter name. What is it?arrow_forwardWhich is TRUE? A. The carbonyl compound got oxidized by the Grignard reagent. B. The product as it is shown is incorrect since the alkene moieties are also expected to react. C. The methyl magnesium bromide acts as the electrophile. D. The product is not expected to undergo tautomerization since it is not an enol E. The secondary alcohol product results from the reduction of the carbonyl starting material.arrow_forwardAn activator molecule like DCC is important to create a good leaving group from a -COOH functional group. A. True B. Falsearrow_forward
- The compound shown below is the product of a Claisen condensation. Draw structural formulas for the reactants: ester and enolate ion. Assume all esters to be ethyl esters. Do not include counter-ions, e.g., Na+, I-, in your answer. Draw the enolate ion in its carbanion form. 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_forwardA small amount of another organic product is formed in a Williamson ether synthesis. What is this product when the alkyl halide used in the synthesis of butyl propyl ether is a. propyl bromide? b. butyl bromide?arrow_forwardI need help with part K. Which was the formula of the acetal product?arrow_forward
- What would be the organic product for each reaction?arrow_forwardThe formation of cyanohydrin from a ketone is an example of A. electrophilic addition B. nucleophilic addition C. nucleophilic substitution D. electrophilic substitution E. none of the abovearrow_forwardIdentify the appropriate nucleophile and alkyl halide substrate to prepare this ether: Structure of the alkyl halide substrate? Structure of the nucleophile?arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Enzymes - Effect of cofactors on enzyme; Author: Tutorials Point (India) Ltd;https://www.youtube.com/watch?v=AkAbIwxyUs4;License: Standard YouTube License, CC-BY
Enzyme Catalysis Part-I; Author: NPTEL-NOC IITM;https://www.youtube.com/watch?v=aZE740JWZuQ;License: Standard Youtube License