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 functional group. The prefix with locant number indicates the number of substituents and their respective position at the main chain or 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 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 - ketone. The prefixes
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 & MECHANISM
- 1.) What is the compound's systematic name? (A) 5-butyl-3,4-dimethylnonane (B) 5-butyl-3,4-dimethyloctane (C) 5,5-dibutyl-3,4-dimethylpentane (D) 5-butyl-6,7-dimethylpentane (E) none of the abovearrow_forward1) Provide the name for each structure shown. NO ₂ 2) Draw the structure of the molecule with the following name: a) (1R, 3S)-Cyclopent-4-ene-1,3-diol b) (2R, 3Z)-3-Chloro-2phenylhex-3-enal c) (2E,4Z)-Hepta-2,4,6-trienoic acid d) (3R, 4E)-3-isopropyl-6-oxohex-4-enenitrile H₂C NH CH3 CH3 H₂N CH3arrow_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
- Give each of the following structures an IUPAC name. (a) (b) H3C H3C² Н2 ОН HC. H2 Н, ОН CH3 (c) (d) НО НО Н, Н, CH ОН C H2 ОН НС. OH CH3arrow_forwardDerive an IUPAC name for the following (cyclo)alkenes. (Do not use cis/trans in your names. Use only the (E)/(Z) designations for double bond stereochemistry. It is not necessary to use italics in writing compound names.) (a) (b) my Xarrow_forwardCompound D undergoes a reaction with hydrogen bromide, HBr to produce 2-bromobutane. D exists as cis-trans isomers and decolourises bromine solution in methylene chloride, CH2Cl2. (i) Draw and name the structure of compound D. (ii) Draw two (2) constitutional isomers of compound D.arrow_forward
- The following names are incorrect. What is wrong with each?(a) Pentan-1-one(b) 4-Methylpentan-3-one(c) Butan-3-onearrow_forwardWrite the IUPAC name for each compound, including the designation of configuration. Do not worry about italics, however syntax is important. (a) Br (b) (S)-2-bromobutane Br H3C. (c) 1-bromo-4-methylcyclohexane (d) 3-chlorocyclohexenearrow_forwardGive the IUPAC names (including E,Z and R,S designations).arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning