Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 27.SE, Problem 13VC
Identify the following fatty acid, and tell whether it is more likely to be found in peanut oil or in red meat:
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Hyaluronic acid, a component of connective tissue, is the fluid that lubricates joints. It is a polymer of alternating N-acetyl-d-glucosamine and d-glucuronic acid subunits joined by β-1,3'-glycosidic linkages. Draw a short segment of hyaluronic acid.
1. Some marine plankton contain triacylglycerols formed from the polyunsaturated fatty acid (PUFA) such as: CH3CH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CHCH2COOH
a) Draw the skeletal structure of the given PUFA showing the preffered stereogenic arrangement for a naturally-occuring lipid at each double bond.
b) Write the systematic name of the fatty acid.
c) What type of omega-n acid is this fatty acid?
d) Would you expect this fatty acid to be a soild or liquid at room temperature?
Linolenic acid and stearidonic acid are omega-3 fatty acids, unsaturated fatty acids that contain the first double bond located at C3, when numbering begins at the methyl end of the chain. Predict how the melting point of stearidonic acid compares with the melting points of linolenic and stearic acids. A current avenue of research is examining the use of soybean oil enriched in stearidonic acid as a healthier alternative to vegetable oils that contain fewer degrees of unsaturation.
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...
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- Eleostearic acid, C18H30O2, is a rare fatty acid found in the tung oil used for finishing furniture. On ozonolysis followed by treatment with zinc, eleostearic acid furnishes one part pentanal, two parts glyoxal (OHC-CHO), and one part 9-oxononanoic acid [OHC(CH2)7CO2H]. What is the structure of eleostearic acid?arrow_forwardLinoleic acid is shown below. What makes this fatty acid particularly susceptible to autoxidation? 1. The red CH bond has a low bond dissociation energy because it is doubly allylic. 2. The red CH bond has a high bond dissociation energy because it is doubly allylic. 3. The red CH bond is the most accessible to reaction with O2 because it is the least sterically crowded CH bond. 4. Both 2 and 3.arrow_forwardBetamethasone is a synthetic anti-inammatory steroid used as a topical cream for itching. Betamethasone is derived from cortisol, with the following structural additions: a C=C between C1 and C2, a uorine at C9, and a methyl group at C16. The configuration at C9 is R, and the configuration at C16 is S. Draw the structure of betamethasone.arrow_forward
- identify which has the lowest pka value. use aromatcity concepts to explain why.arrow_forwardCalculate the theoretical yield of 2mL of vegetable oil saponification reaction with 2mL of 6M NaOH and 40mL of saturated salt solution(NaCl). GIVENS: density of the oil = 0.9 g/mL each fatty acid side chain of the oil has 18 C atoms (C_18: the carbonyl carbon, plus a C_17 carbon chain). Assume an average of one unsaturation per side chain.arrow_forwardCompound A boils at 25 C Compound B boils at 80 C Which has the strong IMFs? OB O Aarrow_forward
- a. Draw a three-dimensional structure for the following steroid. b. What is the structure of the single stereoisomer formed by reduction of this ketone with H2, Pd-C? Explain why only one stereoisomer is formed.arrow_forwardWhen talking about the compound Gal(Beta 1-4) Glc, What carbon involved in glycoside bond? What isomerization? What anomeric still free?arrow_forwardwhat is the heat combustion of C2H5OH at 25C?arrow_forward
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