Organic Chemistry - Owlv2 Access (4 Term)
9th Edition
ISBN: 9781305867659
Author: McMurry
Publisher: Cengage
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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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a) Give the chemical structure for each of the following compound:
(i) 4-hydroxybenzoic acid (ii) 2-hexene
(iii) chlorocyclohexane
(iv) 2,5-dichloroheptane
b) Prostaglandin are a group of C20 lipids and can be found in small amounts in all
body tissues and fluids.
(1) Put an asterisk on all the chiral carbon(s) present in the chemical structure of
prostaglandin E.
(II) Do you expect prostaglandin to be acidic or basic?
(III) Circle the functional group that is responsible for the acidity / basicity.
ali se odno
HO
OH
HO
Prostaglandin E
(a) Draw a skeletal structure of the anabolic steroid 4-androstene-3,17-dione, also called “andro,” from the following description. Andro contains the tetracyclic steroid skeleton with carbonyl groups at C3 and C17, a double bond between C4 and C5, and methyl groups bonded to C10 and C13. (b) Add wedges and dashed wedges for all stereogenic centers with the following information: the configuration at C10 is R, the configuration at C13 is S, and all substituents at ring fusions are trans to each other.
Draw the line-bond formula of an ester in jojoba wax formed from arachidic acid, a 20-carbon saturated fatty acid, and 1-docosanol, CH3(CH2)21OHCH3(CH2)21OH.
Chapter 27 Solutions
Organic Chemistry - Owlv2 Access (4 Term)
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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- (a) Draw a skeletal structure of the anabolic steroid methenolone from the following description. Methenolone contains the tetracyclic steroid skeleton with a carbonyl group at C3, a hydroxyl at C17, a double bond between C1 and C2, and methyl groups bonded to C1, C10, and C13. (b) Add wedges and dashed wedges for all stereogenic centers with thefollowing information: the configuration at C10 is R, the configuration at C13 is S, the configuration at C17 is S, and all substituents at ring fusions are trans to each other. (c) Draw the structure of Primobolan, the product formed when methenolone is treated with CH3(CH2)5COCl and pyridine. Primobolan is an anabolic steroid that can be taken orally or by injection and has been used illegally by well-known Major League Baseball players.arrow_forwardIdentify the functional groups in two drugs, atenolol and donepezil. Atenololis a β (beta) blocker, a drug used to treat hypertension (high bloodpressure), and donepezil (trade name Aricept) is used to treat mild tomoderate dementia associated with Alzheimer's disease.arrow_forwardCycloserine is an antibiotic isolated from the microbe Streptomyces orchidaceous. It is used in conjunction with other drugs for the treatment of tuberculosis: S H-N NH₂ What is the molecular formula of this compound? Enter your answer in form of CxHyN₂Ow.arrow_forward
- 15.15 Draw the structure or give the name of each compound: (a) 2,3-dimethyloctane (b) 1-ethyl-3-methylcyclohexane CH3 (с) CH;—СН,——сH—CH—СH (d) CH3 ČH2-CH3 15.16 Draw the structure or give the name of each compound: (a) (b) НаС. CH3 CH3 (c) 1,2-diethylcyclopentane (d) 2,4,5-trimethylnonanearrow_forwardEleostearic 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_forwardGive the general classification of each compound.(a) glyceryl tripalmitatesodium lauryl sulfate (in shampoo)CH3 (CH2)10 CH2 O S O– Na+OO(b) tetradecyl octadecanoateCH3 (CH2)13 O C (CH2)16 CH3arrow_forward
- Convert the ball-and-stick model of androsterone to (a) a skeletal structure using wedges and dashed wedges around all stereogenic centers; and (b) a three-dimensional representation using chair cyclohexane rings.arrow_forwardFour stereoisomers exist for 3-penten-2-ol. (a) Explain how these four stereoisomers arise. (b) Draw the stereoisomer having the E configuration about the carbon-carbon double bond and the R configuration at the chiral center.arrow_forwardDescribe each highlighted bond in terms of the overlap of atomic orbitals. and Draw the structures of ALL of the aldehydes with the molecular formula C5H10O that contain a 5-carbon chain.arrow_forward
- (b) For the following reactions, draw structures (including any stereoisomers) for the products A-C. 1. LIAIH4 2. H30arrow_forward(9) How many chiral centers are present in a molecule of 1,3-dimethylcyclohexane? (C) 2 (D) 3 1 (A) O (10) What is the percent composition of a mixture of (S)-(+)-2-butanol, [a] = +13.52°, and (R)-(-)-2-butanol, [a] = -13.52°, with a specific rotation [a]D = -6.76° (A) 75%R 25%S (B) 25%R 75%S (C) 50%R 50%S 67%R 33%Sarrow_forwardIdentify which of the statements is/are correct. (i) The molecular formula of the smallest aldehyde is C3H6O, and that of the smallest ketone is also C3H6O. (j) The molecular formula of the smallest carboxylic acid is C2H4O2.arrow_forward
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