Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 27.SE, Problem 41AP
Interpretation Introduction
Interpretation:
Given that vaccenic acid, C18H34O2, gives heptanal and 11-oxoundecanoic acid [OHC(CH2)9COOH] on ozonolysis. It is converted into lactobacillic acid when treated with CH2I2/Zn(Cu). The structures of both vaccenic acid and lactobacillic acids are to be given.
Concept introduction:
Ozonolysis followed by zinc treatment cleaves the double bond in an
To give:
The structures of both vaccenic acid and lactobacillic acids.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Isoerythrogenic acid, C18H26O2, is a acetylic fatty acid that turns vivid vle on exposure to UV light. On Catalytic hydrogenation over a palladium catalyst, five molar equivalents of hydrogen are absorbed, and stearic acid
Stearolic acid, C18H32O2, yields stearic acid on catalytic hydrogenation and undergoes oxidative cleavage with ozone to yield nonanoic acid and nonanedioic acid. What is the structure of stearolic acid?
When an extract of parsley seed is saponified and acidified, one of the fatty acids isolated is petroselenic acid, formulaC18H34O2. Hydrogenation of petroselenic acid gives pure stearic acid. When petroselenic acid is treated with warmpotassium permanganate followed by acidification, the only organic products are dodecanoic acid and adipic acid. TheNMR spectrum shows absorptions of vinyl protons split by coupling constants of 7 Hz and 10 Hz. Propose a structure forpetroselenic acid, and show how your structure is consistent with these observations.2
Chapter 27 Solutions
Organic Chemistry
Ch. 27.1 - Carnauba wax, used in floor and furniture...Ch. 27.1 - Draw structures of glyceryl tripalmitate and...Ch. 27.2 - Prob. 3PCh. 27.2 - Write the saponication reaction of glyceryl...Ch. 27.4 - Prob. 5PCh. 27.5 - Prob. 6PCh. 27.5 - Prob. 7PCh. 27.6 - Draw the following molecules in chair...Ch. 27.6 - Lithocholic acid is an A–B cis steroid found in...Ch. 27.7 - Prob. 10P
Ch. 27.SE - Prob. 11VCCh. 27.SE - Propose a biosynthetic pathway for the...Ch. 27.SE - Identify the following fatty acid, and tell...Ch. 27.SE - Prob. 14MPCh. 27.SE - Prob. 15MPCh. 27.SE - Prob. 16MPCh. 27.SE - Prob. 17APCh. 27.SE - Fats can be either optically active or optically...Ch. 27.SE - Prob. 19APCh. 27.SE - Show the products you would expect to obtain from...Ch. 27.SE - Draw a Newman projection along the C2-C3 bond of...Ch. 27.SE - The plasmalogens are a group of lipids found in...Ch. 27.SE - Prob. 23APCh. 27.SE - Prob. 24APCh. 27.SE - Prob. 25APCh. 27.SE - Prob. 26APCh. 27.SE - Prob. 27APCh. 27.SE - Prob. 28APCh. 27.SE - Prob. 29APCh. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Prob. 34APCh. 27.SE - Draw the most stable chair conformation of...Ch. 27.SE - Draw the most stable chair conformation of...Ch. 27.SE - Prob. 37APCh. 27.SE - Prob. 38APCh. 27.SE - Prob. 39APCh. 27.SE - What product would you obtain by reduction of...Ch. 27.SE - Prob. 41APCh. 27.SE - Eleostearic acid, C18H30O2, is a rare fatty acid...Ch. 27.SE - Prob. 43APCh. 27.SE - Prob. 44APCh. 27.SE - Propose a synthesis of diethylstilbestrol (Problem...Ch. 27.SE - Prob. 46APCh. 27.SE - Cembrene, C20H32, is a diterpenoid hydrocarbon...Ch. 27.SE - α-Fenchone is a pleasant-smelling terpenoid...Ch. 27.SE - Prob. 49APCh. 27.SE - Propose a mechanism for the biosynthesis of the...
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 an extract of parsley seed is saponified and acidified, one of the fatty acids isolated is petroselenic acid, formulaC18H34O2. Hydrogenation of petroselenic acid gives pure stearic acid. When petroselenic acid is treated with warmpotassium permanganate followed by acidification, the only organic products are dodecanoic acid and adipic acid. TheNMR spectrum shows absorptions of vinyl protons split by coupling constants of 7 Hz and 10 Hz. Propose a structure forpetroselenic acid, and show how your structure is consistent with these observations.arrow_forwardMyristoleic acid, C14H26O2, yields myristic acid on catalytic hydrogenation and undergoes oxidative cleavage with ozone to yield pentanoic acid and nonanedioic acid. Draw the structure of Myristoleic acid.arrow_forwardFollowing is a retrosynthetic analysis for the synthesis of the herbicide (S)-Metolachlor from 2-ethyl-6-methylaniline, chloroacetic acid, acetone, and methanol. Show reagents and experimental conditions for the synthesis of Metolachlor from these four organic starting materials. Your synthesis will most likely give a racemic mixture. The chiral catalyst used by Novartis for reduction in Step 2 gives 80% enantiomeric excess of the S enantiomer.arrow_forward
- When the gum of the shrub Sterculia setigera is subjected to acidic hydrolysis, one of the water-soluble components of thehydrolysate is found to be tagatose. The following information is known about tagatose:(1) Molecular formula C6H12O6(2) Undergoes mutarotation.(3) Does not react with bromine water.(4) Reduces Tollens reagent to give d-galactonic acid and d-talonic acid.(5) Methylation of tagatose (using excess CH3 I and Ag2O) followed by acidic hydrolysis gives1,3,4,5-tetra-O-methyltagatose.(a) Draw a Fischer projection structure for the open-chain form of tagatose.(b) Draw the most stable conformation of the most stable cyclic hemiacetal form of tagatosearrow_forwardAn unknown hydrocarbon A with the formula C6H12 reacts with 1 molar equivalent ofH2 over a palladium catalyst. Hydrocarbon A also reacts with OsO4 to give diol B. When oxidized with KMnO4 in acidic solution, A gives two fragments. One fragmentis propanoic acid, CH3CH2CO2H, and the other fragment is ketone C. What are thestructures of A, B, and C? Write all reactions and show your reasoning.arrow_forwardTreatment of salicylaldehyde (2-hydroxybenzaldehyde) with bromine in glacial acetic acid at 0°C gives a compound with the molecular formula C7H4Br2O2, which is used as a topical fungicide and antibacterial agent. Propose a structural formula for this compoundarrow_forward
- A compound A, C7H12, was found to be optically active. On catalytic reduction over platinum catalyst, 2 equivalents of hydrogen were absorbed, yielding compound B, C7H16. On ozonolysis of A, two fragments were obtained. One fragment was identified as acetic acid. The other fragment, compound C, was an optically active carboxylic acid, C5H10O2. Write the reactions and draw structures for A, B and C.arrow_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_forwardCompound J, C16H16Br2, is optically active. On treatment with strong base, compounds K and L (each C16H14) are formed; K and L each absorb only 2 equivalents of hydrogen when reduced over a Pd/C catalyst. Compound K reacts with ozone to give phenylacetic acid (C6H5CH2COOH), while similar treatment of L gives 2 products. One product, M, is an aldehyde with formula C7H6O; the other product is glyoxal (CHO)2. Draw the structure of compound L.arrow_forward
- Two moles of organic compound ‘A’ on treatment with a strong base gives two compounds ‘B’ and ‘C’. Compound ‘B’ on dehydrogenation with Cu gives ‘A’ while acidification of ‘C’ yields carboxylic acid ‘D’ with molecular formula of CH2O2. Identify the compounds A, B, C and D and write all chemical reactions involved.arrow_forward4. 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_forwardGive the expected organic product when phenylacetic acid, PhCH2COOH, is treated with reagent Q.) SOCl2arrow_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