Concept explainers
Videos
The antipsychotic drug flupentixol is prepared by the following scheme:
a)
The alkyl chloride, structure of D has to be identified and R and S configuration has to be assigned for the products.
Concept introduction:
R and S nomenclature: it is used to assign the molecule using CIP rules.
The CIP rules are as follows:
Select the chiral carbon and assign the numbers according to the decreasing atomic mass of atoms attached to it.
If the numbering follows clockwise direction then the molecule is termed as R and if it follows anti-clockwise direction then molecule is termed as S.
Chiral: A molecule is non superimposable on its mirror image is called chiral molecule.
Four different atoms attached to a carbon atom is called chiral molecule.
Isomer: A molecule having the same molecular formula but with different chemical structure is called isomer.
Stereoisomers: Stereoisomers are molecules that have the same molecular formula and they differ only in arrangement of atom in three-dimensional space.
Enantiomers: A compound which is non-superimposable mirror image is called enantiomers.
Diastereomers: A compound which is non-superimposable and non-mirror image is called diastereomers.
Racemic mixture: A racemic mixture is simply a mixture containing an equal amount of each enantiomer.
Achiral: A molecule is superimposable on its mirror image is called achiral molecule.
Answer to Problem 81AP
The reaction is given below,
Explanation of Solution
Given information:
The given reactant shown below,
The given compound (A) reacts with chloro propanol gives the compound (C).
The reaction is given below,
The alkyl chloride, structure of D is given and R and S configuration is assigned for the products.
b)
Interpretation:
The alkyl chloride, structure of D has to be identified and R and S configuration has to be assigned for the products.
Concept introduction:
R and S nomenclature: it is used to assign the molecule using CIP rules.
The CIP rules are as follows:
Select the chiral carbon and assign the numbers according to the decreasing atomic mass of atoms attached to it.
If the numbering follows clockwise direction then the molecule is termed as R and if it follows anti-clockwise direction then molecule is termed as S.
Chiral: A molecule is non superimposable on its mirror image is called chiral molecule.
Four different atoms attached to a carbon atom is called chiral molecule.
Isomer: A molecule having the same molecular formula but with different chemical structure is called isomer.
Stereoisomers: Stereoisomers are molecules that have the same molecular formula and they differ only in arrangement of atom in three-dimensional space.
Enantiomers: A compound which is non-superimposable mirror image is called enantiomers.
Diastereomers: A compound which is non-superimposable and non-mirror image is called diastereomers.
Racemic mixture: A racemic mixture is simply a mixture containing an equal amount of each enantiomer.
Achiral: A molecule is superimposable on its mirror image is called achiral molecule.
Answer to Problem 81AP
The Grignard reagent is given below,
Explanation of Solution
Given information:
The given reactant shown below,
The Grignard reagent is given below,
The compound (c) reaction with thionyl chloride gives chlorinated compound, then it is reacting with magnesium gives the Grignard reagent (D).
The alkyl chloride, structure of D is given and R and S configuration is assigned for the products.
c)
Interpretation
The alkyl chloride, structure of D has to be identified and R and S configuration has to be assigned for the products.
Concept introduction:
R and S nomenclature: it is used to assign the molecule using CIP rules.
The CIP rules are as follows:
Select the chiral carbon and assign the numbers according to the decreasing atomic mass of atoms attached to it.
If the numbering follows clockwise direction then the molecule is termed as R and if it follows anti-clockwise direction then molecule is termed as S.
Chiral: A molecule is non superimposable on its mirror image is called chiral molecule.
Four different atoms attached to a carbon atom is called chiral molecule.
Isomer: A molecule having the same molecular formula but with different chemical structure is called isomer.
Stereoisomers: Stereoisomers are molecules that have the same molecular formula and they differ only in arrangement of atom in three-dimensional space.
Enantiomers: A compound which is non-superimposable mirror image is called enantiomers.
Diastereomers: A compound which is non-superimposable and non-mirror image is called diastereomers.
Racemic mixture: A racemic mixture is simply a mixture containing an equal amount of each enantiomer.
Achiral: A molecule is superimposable on its mirror image is called achiral molecule.
Answer to Problem 81AP
The pair of enantiomers is given below,
Explanation of Solution
Given information:
The given reactant shown below,
The pair of enantiomers is given below,
The compound (D) reaction with compound (E) gives enantiomer of corresponding products.
The alkyl chloride, structure of D is given and R and S configuration is assigned for the products.
d)
Interpretation:
The alkyl chloride, structure of D has to be identified and R and S configuration has to be assigned for the products.
Concept introduction:
R and S nomenclature: it is used to assign the molecule using CIP rules.
The CIP rules are as follows:
Select the chiral carbon and assign the numbers according to the decreasing atomic mass of atoms attached to it.
If the numbering follows clockwise direction then the molecule is termed as R and if it follows anti-clockwise direction then molecule is termed as S.
Chiral: A molecule is non superimposable on its mirror image is called chiral molecule.
Four different atoms attached to a carbon atom is called chiral molecule.
Isomer: A molecule having the same molecular formula but with different chemical structure is called isomer.
Stereoisomers: Stereoisomers are molecules that have the same molecular formula and they differ only in arrangement of atom in three-dimensional space.
Enantiomers: A compound which is non-superimposable mirror image is called enantiomers.
Diastereomers: A compound which is non-superimposable and non-mirror image is called diastereomers.
Racemic mixture: A racemic mixture is simply a mixture containing an equal amount of each enantiomer.
Achiral: A molecule is superimposable on its mirror image is called achiral molecule.
Answer to Problem 81AP
The compound (F) undergoes hydrolysis reaction gives E and Z isomers of corresponding products.
Explanation of Solution
Given information:
The given reactant shown below,
The compound (F) undergoes hydrolysis reaction gives E and Z isomers of corresponding products.
The alkyl chloride, structure of D is given and R and S configuration is assigned for the products.
Want to see more full solutions like this?
Chapter 11 Solutions
EP ORGANIC CHEMISTRY,24 MONTH-OWLV2
- Denote the dipole for the indicated bonds in the following molecules. ✓ H3C CH3 B F-CCl3 Br-Cl H3C —Si(CH3)3 CH3 OH HO HO H HO OH vitamin Carrow_forward(a) What is the hybridization of the carbon in the methyl cation (CH3*) and in the methyl anion (CH3)? (b) What is the approximate H-C-H bond angle in the methyl cation and in the methyl anion?arrow_forward10:16 ☑ Vo)) Vo) 4G LTE 76% Complete the following reaction by identifying the principle organic product of the reaction. HO OH ↑ CH2N2 OH ? ○ A. 01 N₂H2C OH ОН B. HO OCH3 OH ○ C. HO OH ŎCH₂N2 ○ D. H3CO OH он Quiz navigation 1 2 3 4 5 11 12 Next page 10 6 7 8 9 10arrow_forward
- Which one of the following statements explain why protecting groups are referred to as “a necessary evil in organic synthesis”? Question 12Select one or more: A. They increase the length and cost of the synthesis B. Every synthesis employs protecting groups C. Protecting group have no role to play in a synthesis D. They minimize the formation of side productsarrow_forwardWhich of the following attributes is a key advantage of the chiral auxiliary approach over the chiral pool approach in asymmetric synthesis? Question 10Select one: A. Chiral auxiliaries are cheaper than chiral pool substrates B. Chiral auxiliary can be recovered and recycled unlike chiral pool substrates. C. The use of chiral auxiliaries provide enantiopure products, while chiral pool reactions are only enantioselective D. The chiral auxiliaries are naturally occurring and do not require synthesisarrow_forwardIn the following molecule, indicate the hybridization and shape of the indicated atoms. CH3 CH3 H3C HO: CI:arrow_forward
- Which of the following are TRUE about linear syntheses? Question 7Select one: A. They are easier to execute B. They are the most efficient strategy for all syntheses C. They are generally shorter than convergent syntheses D. They are less versatile compared to convergent synthesesarrow_forwardWhich of the following characteristics is common among chiral pool substrates? Question 4Select one: A. They have good leaving groups B. They are all achiral C. All have a multiplicity of chiral centres D. They have poor leaving groupsarrow_forwardDetermine whether the following reaction is an example of a nucleophilic substitution reaction: H NO2 H+ NO 2 + Molecule A Molecule B Is this a nucleophilic substitution reaction? If this is a nucleophilic substitution reaction, answer the remaining questions in this table. What word or two-word phrase is used to describe the role Molecule A plays in this reaction? What word or two-word phrase is used to describe the role Molecule B plays in this reaction? Use a 6 + symbol to label the electrophilic carbon that is attacked during the substitution. Highlight the leaving group on the appropriate reactant. O Yes ○ No ☐ 0 dx 000 HE ?arrow_forward
- Draw the major organic product of the Bronsted acid-base reaction. Include all lone pairs and charges as appropriate. Ignore any counterions. :0: NaOH Harrow_forward5. Calculate the total amount of heat transferred as 50 g of wat Specific heat H₂O (g) 2.00 J/g°C -10 °C. Specific heat H₂O (1) Specific heat H₂O (s) 4.18 J/g°C 2.11 J/g°C Heat of vaporization 2260 J/g Heat of fusion 334 J/g Melting point 0°C 6. Calculate the total amount of heat transferred as 25 g of water is heated from 50 °C to 100 °C as a gas. Boiling point 100 °Carrow_forwardCalculate the total amount of heat transferred as 50 g of Water -10°C. Calculate the total amount of heat transferred as 25 g of water is heated from 50°C to 100°C as a gas. \table[[Specific heat H₂O(g), 2.00°C Η 2 g 5. Calculate the total amount of heat transferred as 50 g of wat Specific heat H₂O (g) 2.00 J/g°C -10 °C. 4.18 J/g°C 2.11 J/g°C 2260 J/g 334 J/g Specific heat H₂O (1) Specific heat H₂O (s) Heat of vaporization Heat of fusion Melting point 6. Calculate the total amount of heat transferred as 25 g of water is heated from 50 °C to 100 °C as a gas. Boiling point 100 °C 0°Carrow_forward
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning