Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Textbook Question
Chapter 16, Problem 16.26P
Wittig reactions with the following α-chloroethers can be used for the synthesis of
- (a) Draw the structure of the triphenylphosphonium salt and Wittig reagent formed from each chloroether.
- (b) Draw the structural formula of the product formed by treating each Wittig reagent with cyclopentanone. Note that the
functional group is an enol ether or, alternatively, a vinyl ether. - (c) Draw the structural formula of the product formed on acid-catalyzed hydrolysis of each enol ether from part (b).
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
The odor of ripe bananas and many other fruits is due to the presence of esters. For example: Banana oil (isopentyl acetate)
(a) Write the name (common or IUPAC) of the ester responsible for the fragrance of the following: pineapple, orange, apple, peach, & lavender
(b) Choose one fragrant from (a) and name the alcohol and the carboxylic acid needed to synthesize this ester.
(c) Show the detailed mechanism of the Fischer Esterification reaction that will be involved in the synthesis of the fragrant you have chosen in part (a).
Ethyl butyrate, CH3CH2CH2CO2CH2CH3CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring.
It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+H+):
CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l)
Part A
Given 7.30 gg of butanoic acid and excess ethanol, how many grams of ethyl butyrate would be synthesized, assuming a complete 100%% yield?
Express your answer in grams to three significant figures.
Part B
A chemist ran the reaction and obtained 5.95 gg of ethyl butyrate. What was the percent yield?
Express your answer as a percent to three significant figures.
Part C
The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0%% yield. How many grams would be produced from 7.30 gg of…
Ethyl butyrate, CH3CH2CH2CO2CH2CH3CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring.
It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+H+):
CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l)
Given 8.45 gg of butanoic acid and excess ethanol, how many grams of ethyl butyrate would be synthesized, assuming a complete 100%% yield?
Express your answer in grams to three significant figures.
A chemist ran the reaction and obtained 5.50 gg of ethyl butyrate. What was the percent yield?
Express your answer as a percent to three significant figures.
The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0%% yield. How many grams would be produced from 8.45 gg of butanoic acid and excess…
Chapter 16 Solutions
Organic Chemistry
Ch. 16.1 - Write the IUPAC name for each compound. Specify...Ch. 16.1 - Write structural formulas for all aldehydes with...Ch. 16.1 - Write the IUPAC name for each compound.Ch. 16.5 - Prob. 16.4PCh. 16.6 - Prob. 16.5PCh. 16.7 - Prob. 16.6PCh. 16.7 - Write a mechanism for the acid-catalyzed...Ch. 16.8 - Prob. 16.8PCh. 16.8 - The given mechanism of transamination reaction is...Ch. 16.8 - The given mechanism of transamination reaction is...
Ch. 16.8 - The given mechanism of transamination reaction is...Ch. 16.8 - Prob. DQCh. 16.8 - Prob. EQCh. 16.8 - The given mechanism of transamination reaction is...Ch. 16.9 - Predict the position of the following equilibrium.Ch. 16.9 - Draw a structural formula for the keto form of...Ch. 16.10 - Prob. 16.11PCh. 16.11 - What aldehyde or ketone gives these alcohols upon...Ch. 16.11 - Prob. 16.13PCh. 16 - Prob. 16.14PCh. 16 - Prob. 16.15PCh. 16 - The infrared spectrum of compound A, C6H12O, shows...Ch. 16 - Following are 1H-NMR spectra for compounds B...Ch. 16 - Draw structural formulas for the product formed by...Ch. 16 - Suggest a synthesis for the following alcohols...Ch. 16 - Show how to synthesize the following alcohol using...Ch. 16 - 1-Phenyl-2-butanol is used in perfumery. Show how...Ch. 16 - Prob. 16.22PCh. 16 - Draw structural formulas for (1) the...Ch. 16 - Show how to bring about the following conversions...Ch. 16 - Prob. 16.25PCh. 16 - Wittig reactions with the following -chloroethers...Ch. 16 - Prob. 16.27PCh. 16 - Prob. 16.28PCh. 16 - 5-Hydroxyhexanal forms a six-membered cyclic...Ch. 16 - Prob. 16.30PCh. 16 - Prob. 16.31PCh. 16 - Propose a mechanism to account for the formation...Ch. 16 - Prob. 16.33PCh. 16 - Prob. 16.34PCh. 16 - Show how to bring about the following conversion.Ch. 16 - A primary or secondary alcohol can be protected by...Ch. 16 - Prob. 16.37PCh. 16 - Prob. 16.38PCh. 16 - Prob. 16.39PCh. 16 - Prob. 16.40PCh. 16 - The following molecule belongs to a class of...Ch. 16 - When cis-2-decalone is dissolved in ether...Ch. 16 - Prob. 16.43PCh. 16 - Prob. 16.44PCh. 16 - The following bicyclic ketone has two -carbons and...Ch. 16 - Propose a mechanism for this reaction.Ch. 16 - The base-promoted rearrangement of an -haloketone...Ch. 16 - If the Favorskii rearrangement of...Ch. 16 - (R)-Pulegone, readily available from pennyroyal...Ch. 16 - (R)-Pulegone is converted to (R)-citronellic acid...Ch. 16 - Starting with cyclohexanone, show how to prepare...Ch. 16 - Show how to convert cyclopentanone to these...Ch. 16 - Prob. 16.53PCh. 16 - Prob. 16.54PCh. 16 - Prob. 16.55PCh. 16 - Following is the structural formula of Surfynol, a...Ch. 16 - Prob. 16.57PCh. 16 - Propose a mechanism for this isomerization.Ch. 16 - Starting with acetylene and 1-bromobutane as the...Ch. 16 - Prob. 16.60PCh. 16 - Prob. 16.61PCh. 16 - Prob. 16.62PCh. 16 - Prob. 16.63PCh. 16 - Prob. 16.64PCh. 16 - All rearrangements we have discussed so far have...Ch. 16 - In dilute aqueous base, (R)-glyceraldehyde is...Ch. 16 - Treatment of -D-glucose with methanol in the...Ch. 16 - Treating a Grignard reagent with carbon dioxide...Ch. 16 - Prob. 16.69PCh. 16 - Prob. 16.70PCh. 16 - Prob. 16.71PCh. 16 - Prob. 16.72PCh. 16 - Write the products of the following sequences of...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Prob. 16.78PCh. 16 - Prob. 16.79PCh. 16 - Prob. 16.80PCh. 16 - Prob. 16.81P
Additional Science Textbook Solutions
Find more solutions based on key concepts
Write the electron configurations far each of the following elements: (a) Sc. (b) Ti. (c) Cr. (d) Fe. (e) Ru
Chemistry by OpenStax (2015-05-04)
Determine [OH], [H+], and the pH of each of the following solutions. a. 1.0 M KCl b. 1.0 M KC2H3O2
Chemistry
Calculate the lattice energy of CaCl2 using a Born-Haber cycle and data from Appendices F and L and Table 7.5. ...
Chemistry & Chemical Reactivity
Classify each example of molecular art as a pure element, a pure compound, or a mixture.
General, Organic, and Biological Chemistry - 4th edition
Problem 11.1 Neopheliosyne B is a novel acetylenic fatty acid isolated from a New Caledonian marine sponge. (a)...
Organic Chemistry
The method to determine the volume of a powered solid, liquid and a rock needs to be determined. Concept introd...
Living By Chemistry: First Edition Textbook
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
- Ethyl butyrate, CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring.It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l). The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0% yield. How many grams would be produced from 8.50 gof butanoic acid and excess ethanol? Express your answer in grams to three significant figures.arrow_forwardEthyl butyrate, CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring.It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l) Given 8.50 g of butanoic acid and excess ethanol, how many grams of ethyl butyrate would be synthesized, assuming a complete 100%yield? Express your answer in grams to three significant figures.arrow_forward(a) Draw the structure of the hemiacetal formed from one mole of benzaldehyde and one mole of ethanol. (b) Draw the structure of the acetal formed from one mole of benzaldehyde and two moles of ethanol. (c) Draw the structure of 2-methoxy-2-butanol. What compounds could you prepare this from?arrow_forward
- Ethyl butyrate, CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring.It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l) a) Given 7.70 g of butanoic acid and excess ethanol, how many grams of ethyl butyrate would be synthesized, assuming a complete 100% yield? b) A chemist ran the reaction and obtained 5.25 g of ethyl butyrate. What was the percent yield? c) The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0% yield. How many grams would be produced from 7.70 g of butanoic acid and excess ethanol?arrow_forward1) The carbon-oxygen double bond present in aldehydes and ketones is very polar. What does this mean and how does it arise? 2) The carbon-oxygen double bond is readily attacked by nucleophiles like cyanide ions or ammonia. (i) What do you understand by the term nucleophile? (ii) Which part of the carbon-oxygen double bond is attractive to nucleophiles? 3) Why is there a difference between aldehydes and ketones in their response to oxidizing agents such as potassium dichromate(VI) solution acidified with dilute sulfuric acid?arrow_forwardAldehydes 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_forward
- Predict the major products formed when benzoyl chloride (PhCOCl) reacts with the following reagents.(a) ethanoarrow_forward(a) Draw the structure of the hemiacetal formed from one mole of benzaldehyde and one mole of ethanol. (b) Draw the structure of the acetal formed from one mole of benzaldehyde and two moles of ethanol. (c) Draw the structure of 2-methoxy-2-butanol. What compounds could you prepare this from? (d) Draw the structure of 3-methoxyl-2-butanol. What functional groups are present? Is this an acetal, a hemiacetal, or neither? Explain. (e) Identify the functional groups in the molecules shown below. Circle any acetals or hemiacetal, and identify which they are. 0-arrow_forwardPredict the major products formed when benzoyl chloride (PhCOCl) reacts with the following reagents.(a) ethanol (b) sodium acetate (c) anilinearrow_forward
- Draw the structural formula of the product of (a) p-methoxybenzaldehyde with each of the following, then do it for (b) 1-phenyl-1-pentanone for each of the following:arrow_forward11) Synthesize 2-methyl-3-hydroxycyclohexone from cyclohexone, methyl iodide, and inorganic precursors.arrow_forwardDimethyl disulfide, CH,S–SCH3, found in the vaginal secretions of female hamsters, acts as a sexual attractant for the male hamster. Write an equation for its synthesis from methanethiol.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
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
07 Physical Properties of Organic Compounds; Author: Mindset;https://www.youtube.com/watch?v=UjlSgwq4w6U;License: Standard YouTube License, CC-BY