Concept explainers
(a)
Interpretation:
The structure from the given IUPAC name with appropriate stereochemistry is to be drawn.
Concept introduction:
The root name in the given IUPAC name suggests the main chain or ring of carbon atoms in the compound. The suffix to root name indicates the highest priority
The stereochemical designation and the locators are enclosed in parenthesis at the very beginning of the name. The stereochemistry at the chiral center is determined by assigning the priorities to the groups attached to the chiral center on the basis of
Answer to Problem E.48P
The structure for IUPAC name
Explanation of Solution
The given IUPAC name is
The root name in this IUPAC name ‘cyclopentan’ represents the main ring of five carbon atoms. The suffix ‘one’ represents the highest priority functional group -
The structure has three chiral centers,
Thus, for absolute configuration
The absolute configuration at
Thus, for absolute configuration
The absolute configuration at
Thus for absolute configuration
Hence, the structure for is
The structure for the given IUPAC name is drawn by identifying the highest priority functional group from the suffix, main chain from root name, and the position for the substituents from the locant with appropriate stereochemistry.
(b)
Interpretation:
The structure from the given IUPAC name with appropriate stereochemistry is to be drawn.
Concept introduction:
The root name in the given IUPAC name suggests the main chain or ring of carbon atoms in the compound. The suffix to root name indicates the highest priority functional group. The prefix with locant number indicates the number of substituents and their respective position at the main chain or at a ring of carbon atoms.
The stereochemical designation and the locators are enclosed in parenthesis at the very beginning of the name. The stereochemistry at the chiral center is determined by assigning the priorities to the groups attached to chiral center on the basis of atomic number of directly bonded atom. If the sequence of priority order
Answer to Problem E.48P
The structure for IUPAC name
Explanation of Solution
The given IUPAC name is
The root name in this IUPAC name ‘pentane’ represents the main chain of five carbon atoms. The suffix ‘dial’ represents the highest priority functional group
The structure has two chiral centers,
Thus, for the absolute configuration
The absolute configuration at
Thus for the absolute configuration
Hence, the structure for
The structure for the given IUPAC name is drawn by identifying the highest priority functional group from the suffix, main chain from root name, and the position for the substituents from the locant with appropriate stereochemistry.
(c)
Interpretation:
The structure from the given IUPAC name with appropriate stereochemistry is to be drawn.
Concept introduction:
The root name in the given IUPAC name suggests the main chain or ring of carbon atoms in the compound. The suffix to root name indicates the highest priority functional group. The prefix with locant number indicates the number of substituents and their respective position at the main chain or at a ring of carbon atoms.
The stereochemical designation and the locators are enclosed in parenthesis at the very beginning of the name. The stereochemistry at the chiral center is determined by assigning the priorities to the groups attached to chiral center on the basis of atomic number of directly bonded atom. If the sequence of priority order
Answer to Problem E.48P
The structure for IUPAC name
Explanation of Solution
The given IUPAC name is
The root name in this IUPAC name ‘heptane’ represents the main chain of seven carbon atoms. The suffix ‘
The structure has two chiral centers,
Thus, for the absolute configuration
The absolute configuration at
Thus, for the absolute configuration
Hence, the structure for
The structure for the given IUPAC name is drawn by identifying the highest priority functional group from the suffix, main chain from root name and the position for the substituents from the locant with appropriate stereochemistry.
(d)
Interpretation:
The structure from the given IUPAC name with appropriate stereochemistry is to be drawn.
Concept introduction:
The root name in the given IUPAC name suggests the main chain or ring of carbon atoms in the compound. The suffix to root name indicates the highest priority functional group. The prefix with locant number indicates the number of substituents and their respective position at the main chain or at a ring of carbon atoms.
The stereochemical designation and the locators are enclosed in parenthesis at the very beginning of the name. The stereochemistry at the chiral center is determined by assigning the priorities to the groups attached to chiral center on the basis of atomic number of directly bonded atom. If the sequence of priority order
Answer to Problem E.48P
The structure for IUPAC name
Explanation of Solution
The given IUPAC name is
The root name in this IUPAC name ‘octa’ represents the main chain of eight carbon atoms. The suffix ‘
The structure has one chiral center,
Thus for the absolute configuration
Hence, the structure for
The structure for the given IUPAC name is drawn by identifying the highest priority functional group from the suffix, main chain from root name and the position for the substituents from the locant with appropriate stereochemistry.
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Chapter E Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
- The IUPAC name of the compound is (a) 5-formylhex-2-en-3-one (b) 5-methyl-4-oxohex-2-en-5-al (c) 3-keto-2-methylhex-5-enal (d) 3-keto-2-methylhex-4-enal The correct statement regarding electrophile is (a) electrophile is a negatively charged species and can form a bond by accepting a pair of electrons from another electrophile (b) electrophiles are generally neutral species and can form a bond by accepting a pair of electrons from a nucleophile (c) electrophile can be either neutral or positively charged species and can form a bond by accepting a pair of electrons from a nucleophile (d) electrophile is a negatively charged species and can form a bond by accepting a pair of electrons from a nucleophile, Which among the given molecules can exhibit tautomerism? Ph Ph I III (a) III only (b) Both I and III (d) Both II and III (c) Both I and II 5) Which of the following biphenyls is optically active? IIarrow_forward1.Name and draw the products of each reaction. (a) 1-propanol + hydrobromic acid → HSO (b) 1-pentanol A HSO (c) N-propylmethanamide + water (d) 3-methyl oct-2-ene + hydrochloric acid - (e) 2-fluoro-2-phenyl butanoic acid + ethanolarrow_forwardDraw the structure that corresponds with each name.(a) 3-ethyloctane (b) 4-isopropyldecane (c) sec-butylcycloheptane(d) 2,3-dimethyl-4-propylnonane (e) 2,2,4,4-tetramethylhexane (f) trans-1,3-diethylcyclopentane(g) cis-1-ethyl-4-methylcyclohexane (h) isobutylcyclopentane (i) tert-butylcyclohexane(j) pentylcyclohexane (k) cyclobutylcyclohexane (l) cis-1-bromo-3-chlorocyclohexanearrow_forward
- Provide the IUPAC name for each of the following compounds. Pay attention to stereochemistry. (c) (a) (Б) О NO2 OH NH2 ОН NH2arrow_forwardDraw the structures of the following molecules: (a) (S)-sec-butylcyclopentane (b) p-benzyltoluene c) (Z)-5-phenyl-3-methyl-3-octenearrow_forwardGiven each of the IUPAC names provided, draw the corresponding structure.(a) 2,4-dicyclopropyl-2-ethoxyhexane(b) 1,2-dichloro-1-(2-methylpropyl)-4-nitrocyclohexane(c) 1,3-dicyclopentyl-1,2,3,4-tetramethoxycyclooctane(d) 1-cyclobutyl-4-(1,1-dimethylethyl)-2,4-dinitrononane(e) 1-(1,1-dimethylbutyl)-2-ethoxy-1,2,3-trinitrocyclobutane(f) 1,2,4-tricyclopropyl-1-(2,2-dichloropentyl)cyclohexane(g) 4-(2-chloro-1-methoxyethyl)-1,1-dinitroheptane(h) 3,3,4-trichloro-1-cyclohexoxy-4-(1,1-dichloroethyl)decanearrow_forward
- Name the following aldehydes and ketones: (a) (b) CH2CH2CHO CH3CH2CCHCH3 CH3 Draw structures corresponding to the following names: (b) 4-Chloropentan-2-one (e) 3-Methylbut-3-enalarrow_forwardDraw 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, Harrow_forwardDraw structures corresponding to the following IUPAC names: (a) 3-Methylbutanal (b) 3-Methylbut-3-enal (c) 4-Chloropentan-2-one (d) Phenylacetaldehyde (e) 2,2-Dimethylcyclohexanecarbaldehyde (f ) Cyclohexane-1,3-dionearrow_forward
- 2. Draw structures corresponding to the following IUPAC names: (d) Phenylacetaldehyde (e) 2,2-Dimethylcyclohexanecarbaldehyde (f ) Cyclohexane-1,3-dionearrow_forwardThe IUPAC name of the compound H- is (a) 5-formylhex-2-en-3-one (b) 5-methyl-4-oxohex-2-en-5-al (c) 3-keto-2-methylhex-5-enal (d) 3-keto-2-methylhex-4-enal ( The correct statement regarding electrophile is (a) electrophile is a negatively charged species and can form a bond by accepting a pair of electrons from another electrophile (b) electrophiles are generally neutral species and can form a bond by accepting a pair of electrons from a nucleophile (c) electrophile can be either neutral or ar positively charged species and can form a bond by accepting a pair of electrons from a nucleophile (d) electrophile is a negatively charged species and can form a bond by accepting a pair of electrons from a nucleophile.. Which among the given molecules can exhibit tautomerism? Ph Ph I II III (a) III only (c) Both I and II (b) Both I and III (d) Both II and III 1) Which of the following biphenyls is optically active?arrow_forwardProvide the IUPAC name for each of the following compounds. Pay close attention to stereochemistry. (a) (b) -NH2 (c) OH ОН NH2 NH2 НО .CI Br. NH2 O,N"arrow_forward
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