Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
expand_more
expand_more
format_list_bulleted
Question
Chapter 16.20, Problem 50P
Interpretation Introduction
Interpretation:
To write the mechanism for the reaction of an acyl chloride with acetate ion to form an acid anhydride.
Concept introduction:
The reaction of an acyl chloride with acetate ion is a nucleophilic substitution reaction. The acetate ion acts as a nucleophile and attacks the carbonyl carbon of the acyl chloride. The attack results in the formation of a tetrahedral intermediate. Some chloride group attached to the carbonyl carbon acts as a leaving group in the reaction and results in the collapse of the tetrahedral intermediate to form the corresponding anhydride.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
く
Predicting the pr
Predict the major products of the following organic reaction:
Δ
Some important notes:
• Draw the major product, or products, of the reaction in the drawing area below.
• If there aren't any products, because no reaction will take place, check the box below the drawing area instead.
• Be sure to use wedge and dash bonds when necessary, for example to distinguish between major products that are
enantiomers.
?
Click and drag to start drawing a structure.
propose synthesis
Explanation
O Conjugated Pi Systems
Deducing the reactants of a Diels-Alder reaction
Can the molecule on the right-hand side of this organic reaction be made in good yield from no more than two reactants, in one
step, by moderately heating the reactants?
?
Δ
If your answer is yes, then draw the reactant or reactants in the drawing area below. You can draw the reactants in any
arrangement you like.
• If your answer is no, check the box under the drawing area instead.
Click and drag to start drawing a structure.
X
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
Knowledge Booster
Similar questions
- Diels Alder Cycloaddition: Focus on regiochemistry (problems E-F) –> match + of thedienophile and - of the diene while also considering stereochemistry (endo).arrow_forwardHELP! URGENT! PLEASE RESOND ASAP!arrow_forwardQuestion 4 Determine the rate order and rate constant for sucrose hydrolysis. Time (hours) [C6H12O6] 0 0.501 0.500 0.451 1.00 0.404 1.50 0.363 3.00 0.267 First-order, k = 0.210 hour 1 First-order, k = 0.0912 hour 1 O Second-order, k = 0.590 M1 hour 1 O Zero-order, k = 0.0770 M/hour O Zero-order, k = 0.4896 M/hour O Second-order, k = 1.93 M-1-hour 1 10 ptsarrow_forward
- Determine the rate order and rate constant for sucrose hydrolysis. Time (hours) [C6H12O6] 0 0.501 0.500 0.451 1.00 0.404 1.50 0.363 3.00 0.267arrow_forwardDraw the products of the reaction shown below. Use wedge and dash bonds to indicate stereochemistry. Ignore inorganic byproducts. OSO4 (cat) (CH3)3COOH Select to Draw ઘarrow_forwardCalculate the reaction rate for selenious acid, H2SeO3, if 0.1150 M I-1 decreases to 0.0770 M in 12.0 minutes. H2SeO3(aq) + 6I-1(aq) + 4H+1(aq) ⟶ Se(s) + 2I3-1(aq) + 3H2O(l)arrow_forward
- Problem 5-31 Which of the following objects are chiral? (a) A basketball (d) A golf club (b) A fork (c) A wine glass (e) A spiral staircase (f) A snowflake Problem 5-32 Which of the following compounds are chiral? Draw them, and label the chirality centers. (a) 2,4-Dimethylheptane (b) 5-Ethyl-3,3-dimethylheptane (c) cis-1,4-Dichlorocyclohexane Problem 5-33 Draw chiral molecules that meet the following descriptions: (a) A chloroalkane, C5H11Cl (c) An alkene, C6H12 (b) An alcohol, C6H140 (d) An alkane, C8H18 Problem 5-36 Erythronolide B is the biological precursor of erythromycin, a broad-spectrum antibiotic. How H3C CH3 many chirality centers does erythronolide B have? OH Identify them. H3C -CH3 OH Erythronolide B H3C. H3C. OH OH CH3arrow_forwardPLEASE HELP! URGENT! PLEASE RESPOND!arrow_forward2. Propose a mechanism for this reaction. ہلی سے ملی N H (excess)arrow_forward
- Steps and explanationn please.arrow_forwardProblem 5-48 Assign R or S configurations to the chirality centers in ascorbic acid (vitamin C). OH H OH HO CH2OH Ascorbic acid O H Problem 5-49 Assign R or S stereochemistry to the chirality centers in the following Newman projections: H Cl H CH3 H3C. OH H3C (a) H H H3C (b) CH3 H Problem 5-52 Draw the meso form of each of the following molecules, and indicate the plane of symmetry in each: OH OH (a) CH3CHCH2CH2CHCH3 CH3 H3C. -OH (c) H3C CH3 (b) Problem 5-66 Assign R or S configurations to the chiral centers in cephalexin, trade-named Keflex, the most widely prescribed antibiotic in the United States. H2N H IHH S Cephalexin N. CH3 CO₂Harrow_forwardSteps and explanationn please.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning