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, Problem 12P
15-16 Which of the following compounds contain stereocenters? (a) 2-Chloropentane(b) 3-Chloropentane (c) 3-Chloro-l-butene(d) 1,2-Dichloropropane
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Draw a three-dimensional structure for each compound, and star all asymmetric carbon
atoms. Draw the mirror image for each structure, and state whether you have drawn a
pair of enantiomers or just the same molecule twice. Build molecular models of any of
these examples that seem difficult to you.
(a)
ОН
(b)
(c)
NH,
ОН
СH—CH—СООН
|
pentan-2-ol
pentan-3-ol
alanine
(d) 1-bromo-2-methylbutane (e) chlorocyclohexane (f) cis-1,2-dichlorocyclobutane
(h)
(i)
H
CH;
"H
H.
H
CH,
H
13 Draw a structural formula for each compound.
(a) 3-Chloropropene
(b) 3-Methylcyclohexene
(c) 1,2-Dimethylcyclohexene
(d) trans-3,4-Dimethyl-3-heptene
(e) Cyclopropene
(f) 3-Hexyne
16-57 Starting with either benzene or toluene, how would you synthesize the
following substances? Assume that ortho and para isomers can be
separated.
(a) 2-Bromo-4-nitrotoluene
(c) 2,4,6-Tribromoaniline
(b) 1,3,5-Trinitrobenzene
(d) m-Fluorobenzoic acid
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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- (a) A phenyl group has the molecular formula CH- and is represented by the symbol Bn. True False (b) Para substituents occupy adjacent carbons on a benzene ring. (c) True False (e) 3-Bromobenzoic acid can be separated into cis and trans isomers. True O False (d) 1-Phenylcyclohexene is a planar molecule. True False Benzene, naphthalene, and phenanthrene are polynuclear aromatic hydrocarbons (PAHs). Truearrow_forward(b) CH2CH3 H2c-c CH3 (а) NaOH CH3 MgBr (c) H3C-c-c CH2CH3 2. H30" CH3 HCI (е) (d) CH3 HCI Ether Etherarrow_forward15-46 Consider Lunesta, a nonbenzodiazepine hypnotic agent (i.e., sleep-inducing drug) that is frequently advertised on TV commercials. Answer the following questions with respect to the given structure: Lunesta Determine the molecular formula for Lunesta. Identify the functional groups present in Lunesta. How many of Lunesta’s rings are aromatic? Fill in the blanks as shown: Lunesta has stereocenter(s) and therefore possible stereoisomer(s). Of the possible stereocenter(s), is/are R and is/are S. Does Lunesta have an enantiomer? Does it have a diastereomer? Which of the following is true about an enantiomer of Lunesta? Identify all that apply: The enantiomer rotates plane-polarized light in the opposite direction as Lunesta. The enantiomer is a mirror image of Lunesta. The enantiomer has the opposite biological effects as Lunesta (i.e., it keeps you awake). Lunesta does not have an enantiomer. Draw an enantiomer of Lunesta. Examine the derivative of the representation of the six-membered ring found in Lunesta. Draw the alternative chair conformations of this ring and label the more stable chair conformation. (Chapter 11)arrow_forward
- 17) Which of the following compounds does not have the molecular formula C6H140? (a) 1-hexanol (b) 2-hexanol (c) 3-methyl-2-pentanol (d) 3-methyl-3-pentanol (e) Cyclohexanolarrow_forwardName each alkene and specify its configuration using the E,Z system. (a) [E-1-chloro-2,3-dimethylpent-2-ene (b) Br (c) 3,4-dimethyl-3-heptene (d) [3-ethyl-2-hexenearrow_forward(a) How will you convert:(i) Benzene to acetophenone (ii) Propanone to 2-Methylpropan-2-ol(b) Give reasons :(i) Electrophilic substitution in benzoic acid takes place at meta position.(ii) Carboxylic acids are higher boiling liquids than aldehydes, ketones and alcohols of comparable molecular masses.(iii) Propanal is more reactive than propanone in nucleophilic addition reactions.arrow_forward
- Draw the structural formulas of the following compounds:(a) 2,4-Dinitroacetophenone(b) 2,4-Dihydroxycyclopentanone(c) 2-Methoxy-2-methylpropane(d) 2,3,4-Trimethylpentan-3-olarrow_forwardHow do you convert:(i) Chlorobenzene to biphenyl(ii) Propene to 1-iodopropane(iii) 2-bromobutane to but-2-enearrow_forwardPredict which member of each group is most soluble in water, and explain the reasons for your predictions.(a) butan-1-ol, pentan-1-ol, or propan-2-ol(b) chlorocyclohexane, cyclohexanol, or cyclohexane-1,2-diol(c) phenol, cyclohexanol, or 4-methylcyclohexanolarrow_forward
- Draw structures for the following compounds: (a) 2,2-dimethylpropane (b) 3-methylheptane (c) 4,5-diethylnonane (d) 4-(1-methylethyl) heptane (e) 5-(1,1-dimethylethyl) nonane (f) ethylcyclobutane (g) 1-ethyl-4-methylcyclohexanearrow_forwardGive IUPAC names of the following compounds and identify the alcohols as primary, secondary or tertiary. (а) CH3 (b) H3C-CH2-CH-OH H3C-C-OH ČH3 ČH3 CH3 H3C-CH2-CH2-Ċ-OH H,Ċ-CH, ČH2 ČH3 (с) (d) CH3 НО (е) .CH3 CH2-CH3 C=CH HO-CH2 H3C (f) НОarrow_forwardThe action of heating one mole of water (containing a trace of acid catalyst) on one mole of compound Y produces one mole of CH,COOH and one mole of CH, CH,NH, The structure of Y is: Select one: O CHCNCCH, CH,CH,NHCH,CH, OH CH CHNHCH,CH, O CHCH,CNHCH; O CH;CH NHÖCH;arrow_forward
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