Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 3.SE, Problem 50AP
Formaldehyde, H2C=O, is known to all biologists because of its usefulness as a tissue preservative. When pure, formaldehyde trimerizes to give trioxane, C3H6O3, which, surprisingly enough, has no carbonyl groups. Only one monobromo derivative (C3H5BrO3) of trioxane is possible. Propose a structure for trioxane.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
In an advanced synthetic chemistry experiment, a researcher prepares a compound, ZY-7, by reacting a ketone (C5H10O) with hydroxylamine (NH2OH), followed by heating in the presence of an acid catalyst. The resulting compound, ZY-7, is then treated with a solution of sodium nitrite (NaNO2) and hydrochloric acid (HCl) at low temperature. Identify the class of compound that ZY-7 most likely belongs to after this series of reactions." A) Amide B) Oxime C) Nitro compound D) Diazonium salt E) Ester Don't use chatgpt please provide valuable answer
Three constitutional isomers of molecular formula C 5H 8O can be converted to 1-pentanol (CH 3CH 2CH 2CH 2CH 2OH) on treatment with two equivalents of H 2 in the presence of a Pd catalyst. Draw the structures of the three possible compounds, all of which contain a carbonyl group
A synthetic organic molecule, G, which contains both aldehyde and ether functional groups, is subjected to a series of reactions in a multi-step synthesis pathway. In the first step, G undergoes a Wittig reaction, leading to the formation of an alkene, H. Subsequently, H is treated with an ozone (O3) reagent followed by a reducing agent in an ozonolysis reaction, resulting in the formation of two different products, I and J. Considering the functional groups present in G and the nature of the reactions involved, what are the most probable structures or functional groups present in products I and J? A. I contains a carboxylic acid group, and J contains an aldehyde group. B. I contains a ketone group, and J contains an alcohol group. C. I and J both contain aldehyde groups. D. I contains an ester group, and J contains a ketone group. Don't use chat gpt.
Chapter 3 Solutions
Organic Chemistry
Ch. 3.1 - Prob. 1PCh. 3.1 - Prob. 2PCh. 3.1 - Identify the functional groups in the following...Ch. 3.2 - Draw structures of the five isomers of C6H14.Ch. 3.2 - Propose structures that meet the following...Ch. 3.2 - Prob. 6PCh. 3.3 - Draw the eight 5-carbon alkyl groups (pentyl...Ch. 3.3 - Identify the carbon atoms in the following...Ch. 3.3 - Prob. 9PCh. 3.3 - Prob. 10P
Ch. 3.4 - Give IUPAC names for the following compounds:Ch. 3.4 - Prob. 12PCh. 3.4 - Name the eight 5-carbon alkyl groups you drew in...Ch. 3.4 - Give the IUPAC name for the following hydrocarbon,...Ch. 3.7 - Make a graph of potential energy versus angle of...Ch. 3.7 - Sight along the C2-C1 bond of 2-methylpropane...Ch. 3.7 - Sight along the C2-C3 bond of 2,3-dimethylbutane,...Ch. 3.7 - Draw a Newman projection along the C2-C3 bond of...Ch. 3.SE - Prob. 19VCCh. 3.SE - Prob. 20VCCh. 3.SE - Draw a Newman projection along the C2-C3 bond of...Ch. 3.SE - Prob. 22APCh. 3.SE - Prob. 23APCh. 3.SE - Propose structures for the following: (a) A...Ch. 3.SE - Prob. 25APCh. 3.SE - Draw the structures of the following molecules:...Ch. 3.SE - Draw structures that meet the following...Ch. 3.SE - Prob. 28APCh. 3.SE - In each of the following sets, which structures...Ch. 3.SE - There are seven constitutional isomers with the...Ch. 3.SE - Prob. 31APCh. 3.SE - Draw compounds that contain the following: (a) A...Ch. 3.SE - Prob. 33APCh. 3.SE - Draw and name all monochloro derivatives of...Ch. 3.SE - Draw structures for the following: (a)...Ch. 3.SE - Prob. 36APCh. 3.SE - Draw a compound that: (a) Has nine primary...Ch. 3.SE - Give IUPAC names for the following compounds:Ch. 3.SE - Name the five isomers of C6H14.Ch. 3.SE - Explain why each of the following names is...Ch. 3.SE - Prob. 41APCh. 3.SE - Consider 2-methylbutane (isopentane). Sighting...Ch. 3.SE - What are the relative energies of the three...Ch. 3.SE - Construct a qualitative potential-energy diagram...Ch. 3.SE - Prob. 45APCh. 3.SE - Draw the most stable conformation of pentane,...Ch. 3.SE - Draw the most stable conformation of...Ch. 3.SE - Prob. 48APCh. 3.SE - Prob. 49APCh. 3.SE - Formaldehyde, H2C=O, is known to all biologists...Ch. 3.SE - Prob. 51APCh. 3.SE - Increased substitution around a bond leads to...Ch. 3.SE - Prob. 53APCh. 3.SE - In the next chapter we'll look at...Ch. 3.SE - We’ll see in the next chapter that there are two...
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
- Three isomeric pentanols with unbranched carbon chains exist. Which of these isomers, upon dehydration at 180C, yields only 1-pentene as a product?arrow_forwardAmines are converted into alkenes by a two-step process called Hofmann elimination. SN2 reaction of the amine with an excess of CH3I in the first step yields an intermediate that undergoes E2 reaction when treated with silver oxide as base. Pentylamine, for example, yields 1-pentene. Propose a structure for the intermediate, and explain why it readily undergoes elimination.arrow_forwardCompound AA has a molecular formula of C3H6O and gives a positiveresult using Tollen’s reagent. The reaction of compound AA with hotacidified potassium permanganate, KMnO4 gives compound BB. Thecatalytic hydrogenation of compound AA with nickel, Ni producedcompound CC. The reaction of compound BB with ethanamine,CH3CH2NH2 produces compound DD I) Draw the structural formula of compounds AA, BB, CC and DD. 2)Name the type of chemical reaction for the formation of compound CC.arrow_forward
- Hydrocarbon X has the formula C6H12.X reacts with one molar equivalent of hydrogen in the presence of a palladium catalyst to form a product having 12 primary hydrogens.Treatment of X with ozone followed by zinc in aqueous acid gives a mixture two aldehydes.What is the structure of X?arrow_forwardCompound A (C11H23Br) is a secondary alkyl halide. On being heated with a solution of sodium ethoxide in ethanol, compound A yielded a mixture of two alkenes B and C, each having molecular formula C11H22. Catalytic hydrogenation of the major isomer B or the minor isomer C gave only 3,5-diethylheptane. Draw structures for compounds A, B, and C consistent with these observations.arrow_forwardPropose the structure of the following: a. An alkane, C6H14 b. A crylic saturated hydrocarbon, C6H12 c. A diene (dialkene), C5H8 d. A keto alkene, C5H8Oarrow_forward
- 4. Compound A has the formula C 8H 8. It reacts rapidly with KMnO 4 to give CO 2 and a carboxylic acid, B (C 7H 6O 2), but reacts with only 1 molar equivalent of H 2 on catalytic hydrogenation over a palladium catalyst. On hydrogenation under conditions that reduce aromatic rings, 4, equivalents of H 2 are taken up and hydrocarbon C (C 8H 16) is produced. What are the structures of A, B, and C.arrow_forward2-bromo-2-methylbutane undergoes hydrolysis reaction with water, H2O toform compound W. Compound X and compound Y are produced when 2-bromo-2-methylbutane undergoes elimination reaction with alcoholic ofsodium hydroxide, NaOH. (i) Draw the structural formula of compounds W, X and Yarrow_forwardAspirin, or 2-acetoxybenzoic acid, (C9H8O4) is often synthesised from salicylic acid.(i) Sketch and discuss any changes in the number of possible structural conformations ofaspirin relative to those of salicylic acid. (ii) Re-draw the structure predicted to be the lowest energy conformation of aspirin,indicating any expected stabilising and destabilising interactions. Justify your choice.arrow_forward
- An optically active monoterpene (compound A) with molecular formula C10H18O undergoes catalytic hydrogenation to form an optically inactive compound with molecular formula C10H20O (compound B). When compound B is heated with acid, followed by reaction with O3 and then with dimethyl sulfide, one of the products obtained is 4-methylcyclohexanone. Give possible structures for compounds A and B.arrow_forwardGrignard reagent is a versatile tool in synthetic organic chemistry. Using bromocyclopentane as a starting material, show how a Grignard reagent, X, is synthesized. Reaction of X with water produces compound Y while treatment in carbon dioxide followed by hydrolysis forms compound Z. 3-methyl-2butanone reacts with X and hydrolyses to yield compound AA. Draw the structural formulae of compounds Y, Z and AA and write the chemical equations respectively.arrow_forwardPropose structures for molecules that fit the following descriptions:(a) An aldehyde with the formula C5H10O(b) An ester with the formula C6H12O2(c) A compound with the formula C3H7NOS that is both anamide and a thiolarrow_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
General, Organic, and Biological ChemistryChemistryISBN:9781285853918Author:H. Stephen StokerPublisher:Cengage Learning
Organic And Biological ChemistryChemistryISBN:9781305081079Author:STOKER, H. Stephen (howard Stephen)Publisher:Cengage Learning,
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
General, Organic, and Biological Chemistry
Chemistry
ISBN:9781285853918
Author:H. Stephen Stoker
Publisher:Cengage Learning
Organic And Biological Chemistry
Chemistry
ISBN:9781305081079
Author:STOKER, H. Stephen (howard Stephen)
Publisher:Cengage Learning,
General Chemistry | Acids & Bases; Author: Ninja Nerd;https://www.youtube.com/watch?v=AOr_5tbgfQ0;License: Standard YouTube License, CC-BY