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Questions and Answers
What is the defining characteristic of the Z isomer?
What is the defining characteristic of the Z isomer?
- Functional groups are on opposite sides of the double bond.
- Functional groups have differing priorities.
- Functional groups are symmetrical around the double bond.
- Functional groups are on the same side of the double bond. (correct)
Which statement best reflects the first step in determining E or Z isomerism using the CIP rules?
Which statement best reflects the first step in determining E or Z isomerism using the CIP rules?
- Higher priority atoms are determined by atomic number.
- Comparisons should be made between all attached atoms.
- Only the first atom attached to the C=C bond is considered. (correct)
- The second atoms must always be considered first.
In determining priority based on the second atoms, which of the following pairs is correctly analyzed in compound A?
In determining priority based on the second atoms, which of the following pairs is correctly analyzed in compound A?
- Bromine is compared to hydrogen. (correct)
- Hydrogen is compared to carbon.
- Chlorine is compared to bromine.
- Carbon is compared to bromine.
What is the consequence of determining that chlorine has a higher priority than hydrogen in the context of E/Z isomerism?
What is the consequence of determining that chlorine has a higher priority than hydrogen in the context of E/Z isomerism?
What conclusion can be drawn if the two highest priority groups in a compound are on the same side of the double bond?
What conclusion can be drawn if the two highest priority groups in a compound are on the same side of the double bond?
Which of the following pairs would NOT allow for E/Z classification due to equal priority?
Which of the following pairs would NOT allow for E/Z classification due to equal priority?
When analyzing compound A, what indicates that the bromine group takes priority over the carbon group?
When analyzing compound A, what indicates that the bromine group takes priority over the carbon group?
How are the CIP priority rules applied when the first attached atoms are the same?
How are the CIP priority rules applied when the first attached atoms are the same?
What does the empirical formula represent?
What does the empirical formula represent?
Which type of isomerism involves molecules with the same molecular formula but different functional groups?
Which type of isomerism involves molecules with the same molecular formula but different functional groups?
What distinguishes a displayed formula from a skeletal formula?
What distinguishes a displayed formula from a skeletal formula?
What is a characteristic of members of a homologous series?
What is a characteristic of members of a homologous series?
In the context of isomerism, what are position isomers?
In the context of isomerism, what are position isomers?
What does E-Z isomerism specifically involve?
What does E-Z isomerism specifically involve?
Which formula follows a systematic pattern for a homologous series?
Which formula follows a systematic pattern for a homologous series?
Which of the following statements is NOT true regarding structural isomers?
Which of the following statements is NOT true regarding structural isomers?
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Study Notes
Introduction to Organic Chemistry
- Nomenclature is the system used to name and represent organic compounds.
- Empirical Formula = The simplest whole number ratio of atoms of each element in a compound.
- Molecular Formula = The true number of atoms of each element in a compound.
- General Formula = All members of a homologous organic series follow the general formula.
- Structural Formula = Shows the structural arrangement of atoms within a molecule.
- Displayed Formula = Shows every atom and every bond in an organic compound.
- Skeletal Formula = Shows only bonds in a compound and any non-carbon atoms.
- Vertices are carbon atoms.
- Hydrogen is assumed to be bonded to them unless stated otherwise.
Homologous Series
- Organic compounds often belong to homologous series.
- Members share a general formula.
- Members react in a similar way.
- Each consecutive member differs by CH2.
- Boiling points increase as chain length increases in homologous series.
Reaction Mechanisms
- Reaction mechanisms show the movement of electrons in a reaction.
- Curly arrows are used to show the movement of electrons.
Isomerism
- Isomers are molecules with the same molecular formula but a different arrangement of atoms.
Structural Isomers
- Structural isomers have a different structural arrangement of atoms.
- They can be straight chains or branched chains.
Position Isomers
- Position isomers have the functional group of the molecule in a different position on the carbon chain.
Functional Group Isomers
- Functional group isomers have a different arrangement of the same molecular formula, resulting in a different functional group.
Stereoisomers
- Stereoisomers have a different spatial arrangement.
- E/Z isomerism occurs when limited rotation around a double carbon bond means that functional groups can either be ‘together’ or ‘apart’.
- The E isomer (german for entgegen meaning apart) has functional groups on opposite sides.
- The Z isomer (german for zusammen meaning together) has functional groups together on the same side of the double bond.
Cahn-Ingold-Prelog (CIP) Priority Rules
- CIP rules determine priority in E/Z isomerism by considering atomic number of the directly bonded atoms.
- The atom with the higher atomic number is prioritized.
- In more complex cases, where the first atom is the same, you need to look at the second atom bonded to the carbon.
- Again, the atom with the higher atomic number is prioritized.
- Determine E or Z by the location (same or opposite sides) of the highest priority groups.
- If highest priority groups are on the same side, then it’s a Z isomer.
- If highest priority groups are on opposite sides, then it’s an E isomer.
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