Introduction To General, Organic, And Biochemistry
12th Edition
ISBN: 9781337571357
Author: Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher: Cengage Learning
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Chapter 14.2, Problem 14.2QC
Problem 15-2 Assign priorities to the groups in each set
II
- —CH2OH and —CH2CH2COH O
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PROBLEM 5-21
Which of the following compounds are chiral? Draw each compound in its most symmetric con-
formation, star (*) any asymmetric carbon atoms, and draw any mirror planes. Label any meso
compounds. You may use Fischer projections if you prefer.
(a)
meso-2,3-dibromo-2,3-dichlorobutane
(b) (±)-2,3-dibromo-2,3-dichlorobutane
(c) (2R,3S)-2-bromo-3-chlorobutane
(d) (2R,3S)-2,3-dibromobutane
(e) (R, R)-2,3-dibromobutane
(f)
H-
HO
CHO
-OH
-H
CH₂OH
H
Br
H.
CH₂
H
CH₂
H
Br
(h) H
Br
CH₂
H
H
CH₂
H
Br
#15 problem F
PROBLEM 3-8
Draw the structures of the following compounds.
(a) 4-(1,1-dimethylethyl)octane
(c) 3,3-diethyl-4-(2,2-dimethylpropyl)octane
(b) 5-(1,2,2-trimethylpropyl)nonane
Chapter 14 Solutions
Introduction To General, Organic, And Biochemistry
Ch. 14.1 - Prob. 14.1QCCh. 14.2 - Problem 15-2 Assign priorities to the groups in...Ch. 14.2 - Problem 15-3 Assign an R or S configuration to the...Ch. 14.3 - Problem 15-4 3-Amino-2-butanol has two...Ch. 14.3 - Prob. 14.5QCCh. 14.3 - Prob. 14.6QCCh. 14 - 15-7 Answer true or false. The cis and trans...Ch. 14 - 15-8 What does the term “chiral” mean? Give an...Ch. 14 - 15-9 What does the term “achiral” mean? Give an...Ch. 14 - 15-10 Define the term “stereoisomer.” Name three...
Ch. 14 - 15-11 In what way are constitutional isomers...Ch. 14 - 15-12 Which of the following objects are chiral...Ch. 14 - Prob. 7PCh. 14 - Prob. 8PCh. 14 - Prob. 9PCh. 14 - Prob. 10PCh. 14 - 15-15 Explain why the carbon of a carbonyl group...Ch. 14 - 15-16 Which of the following compounds contain...Ch. 14 - 15-17 Which of the following compounds contain...Ch. 14 - Prob. 14PCh. 14 - 15-19 Draw the mirror image for each molecule: OH...Ch. 14 - Prob. 16PCh. 14 - 15-21 Answer true or false. For a molecule with...Ch. 14 - Prob. 18PCh. 14 - Prob. 19PCh. 14 - Prob. 20PCh. 14 - Prob. 21PCh. 14 - 15-26 For centuries, Chinese herbal medicine has...Ch. 14 - Prob. 23PCh. 14 - Prob. 24PCh. 14 - Prob. 25PCh. 14 - Prob. 26PCh. 14 - Prob. 27PCh. 14 - Prob. 28PCh. 14 - Prob. 29PCh. 14 - Prob. 30PCh. 14 - 15-35 Following are structural formulas for three...Ch. 14 - Prob. 32PCh. 14 - 15-37 Consider a cyclohexane ring substituted with...Ch. 14 - Prob. 34PCh. 14 - Prob. 35PCh. 14 - Prob. 36PCh. 14 - 15-41 Compound A(C5Hh, is not optically active and...Ch. 14 - Prob. 38PCh. 14 - 15-43 Triamcinolone acetonide, the active...Ch. 14 - 15-44 Consider the structure of the...Ch. 14 - Prob. 41PCh. 14 - 15-46 Consider Lunesta, a nonbenzodiazepine...Ch. 14 - Prob. 43PCh. 14 - Prob. 44P
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- Problem 15-4 3-Amino-2-butanol has two stereocenters (carbons 2 and 3); thus, 22 = 4 stereoisomers are possible for it. 'CHa H-“C-OH 3I h2n—c— h 4ch3 ch3 H-C-OH I H —C—NH2 ch3 ch3 HO-C-H I H — C— NH2 ch3 ch3 HO-C-H I H,N—C-H ch3 Which stereoisomers are pairs of enantiomers? Which sets of stereoisomers are diastereomers?arrow_forwardProblem 12-5 How many stereoisomers are possible for the following unsaturated alcohol? ch3 ch3 ch3 ch3c=chch2ch2c=chch2ch2c=chch2oharrow_forwardPROBLEM 5-16 Which of the following structures represent meso compounds? (a) он (b) OH (c) CH3 (d) H. Br CH3 C' H. H. HO H. HOH H. H. H. H3c-C Brarrow_forward
- Problem 17-7 Identify all hemiacetals and acetals in the following structures and tell whether each is formed from an aldehyde or a ketone. OH (a) (b) CH3OCH2CH2OCH3 (c)arrow_forwardConsidering cis-trans isomers, how many compounds are possible for 1,3,6-octatriene ? CH₂=CH-CH=CH-CH₂-CH=CH-CH3 Submit Answer Retry Entire Group 8 more group attempts rema Previous Nex Savarrow_forwardProblem Three a) Tamoxifen is a breast cancer drug. i) Identify which geometrical isomer it is by assigning a one-letter stereodescriptor: ii) Predict the acid-base behaviour of Tamoxifen and name its functional groups b) i) The Parkinson's disease drug Levodopa is shown. Which one-letter stereodescriptor (S or R) describes its chiral centre? your HO. HO NH₂ OHarrow_forward
- Problem 15-3 Assign an R or S configuration to the single stereocenter in glyceralde- hyde, the simplest carbohydrate (Chapter 20).arrow_forwardPROBLEM 3-24 Draw the most stable conformation of: (a) ethylcyclohexane (c) cis-1-tert-butyl-4-isopropylcyclohexane (b) 3-isopropyl-1, 1-dimethylcyclohexanearrow_forwardPROBLEM 13-3Determine the number of different kinds of protons in each compound. 1-bromo-2-methylbenzene,arrow_forward
- Problem 14-6 Write the common name for each ether.arrow_forwardProblem 3 A student completed the Diels-Alder shown reaction below. OMe Me0 MeO Name: 2-methoxybuta- 1,3-dene Molecular weight. 84.12 Formula C,HD Name methyl prop-2-enoate Molecular weight. 86.09 Formula C,H,0, Name: methy 4-methoxycyclohex-3-ene-1-carboxylate Molecular weig 170.21 Formula C,H O, The student used the following amounts: 3.500g of 2-methoxybuta-1,3-diene • 3.500g of methyl prop-2-enoate T.. The student collected the following materials: 6.230g of crude product (impure product) • 5.8020g of recrystallized product (pure product) Use the information provided above to determine the following: The theoretical yield of the reaction. b. The percent yield of the reaction for the recrystallized product. The percent recovery for the recrystallization step (i.e. from crude to pure product). Clearly show and explain how you determined the limiting reactant. a. C.arrow_forwardProblem 16-1 How many hydrogen atoms does pyrrolidine have? How many does purine have? Write the xnolecular formula of each amine.arrow_forward
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