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Chapter 16: Problem 35

Draw structures for the following compounds: (a) \(p\)-nitrobenzaldehyde (b) \((S)-4\)-methylhexanal (c) \((E)-2\)-butenal (d) \(c i s-2-\) bromocyclopropanecarboxaldehyde

Short Answer

Expert verified
Compounds are drawn with specified positions: (a) p-nitrobenzaldehyde, (b) (S)-4-methylhexanal, (c) (E)-2-butenal, (d) cis-2-bromocyclopropanecarboxaldehyde.

Step by step solution

01

Understanding the Compound Structure

Identify the functional groups and positions on the main structure for each compound listed.
02

Drawing (a) p-nitrobenzaldehyde

Draw a benzene ring. Attach an aldehyde group (-CHO) at the para position (carbon 1), opposite to a nitro group (-NO2) at the para position (carbon 4).
03

Drawing (b) (S)-4-methylhexanal

Draw a hexane chain with 6 carbon atoms. Attach an aldehyde group (-CHO) to the first carbon. Attach a methyl group (-CH3) to the fourth carbon in an (S) configuration, ensuring correct stereochemistry.
04

Drawing (c) (E)-2-butenal

Draw a butene chain with 4 carbon atoms and an aldehyde group (-CHO) at the second carbon. Make sure to represent the double bond between C2 and C3 in the trans (E) configuration.
05

Drawing (d) cis-2-bromocyclopropanecarboxaldehyde

Draw a cyclopropane ring with three carbon atoms. Attach a bromine atom to the second carbon and a carboxaldehyde group (-CHO) to the first carbon. Ensure both substituents are on the same side of the ring (cis configuration).

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Functional Groups
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. They play a crucial role in organic chemistry as they determine the molecule's properties and reactivity.
In the exercise provided:
  • p-nitrobenzaldehyde has two functional groups: an aldehyde group (-CHO) attached to a benzene ring at the para position, and a nitro group (-NO2) at the opposite para position.
  • (S)-4-methylhexanal has an aldehyde group (-CHO) at the first carbon of a hexane chain and a methyl group (-CH3) at the fourth carbon.
  • (E)-2-butenal features an aldehyde group (-CHO) at the second carbon and a double bond between the second and third carbon atoms.
  • cis-2-bromocyclopropanecarboxaldehyde includes a bromine atom and a carboxaldehyde group (-CHO) on a cyclopropane ring.
Understanding these functional groups helps to predict the behavior of these compounds in chemical reactions and their possible applications.
Stereochemistry
Stereochemistry is the study of the spatial arrangement of atoms in molecules and its impact on their chemical behavior. It is crucial in determining how molecules interact with each other and biological systems.
  • (S)-4-methylhexanal is an example of stereoisomerism where the configuration of the chiral center at the fourth carbon is designated as 'S' (from the Latin ‘sinister’, meaning left), indicating its R/S configuration. This configuration dictates how the compound interacts with other chiral molecules.
  • cis-2-bromocyclopropanecarboxaldehyde showcases cis-trans isomerism where the bromine atom and carboxaldehyde group are on the same side of the cyclopropane ring.
Proper representation of stereochemistry in molecular structures is vital for students as it significantly influences the physical and chemical properties of compounds.
IUPAC Nomenclature
The International Union of Pure and Applied Chemistry (IUPAC) nomenclature system provides a standardized way to name chemical compounds. It ensures that each compound has a unique and universally accepted name.
In the given example:
  • p-nitrobenzaldehyde: 'p' stands for the para position on the benzene ring, where the nitro group is opposite the aldehyde group.
  • (S)-4-methylhexanal: 'S' indicates the stereochemistry of the chiral center, while '4-methyl' refers to a methyl group attached to the fourth carbon of the hexane chain, and 'hexanal' signifies an aldehyde group attached to the first carbon.
  • (E)-2-butenal: 'E' denotes the trans configuration of the double bond, with '2-butenal' indicating the position of the aldehyde group on the second carbon of a butene chain.
  • cis-2-bromocyclopropanecarboxaldehyde: 'cis' specifies the orientation of substituents on the cyclopropane ring, with '2-bromo' and 'carboxaldehyde' indicating the groups attached to the carbon atoms.
Learning IUPAC nomenclature helps students accurately communicate and interpret chemical information.
Cis-Trans Isomerism
Cis-trans isomerism (also known as geometric isomerism) occurs due to the restricted rotation around double bonds or within ring structures, leading to different spatial arrangements.
In this exercise:
  • (E)-2-butenal is an example of a trans (E) isomer, where the highest priority substituents (according to Cahn-Ingold-Prelog rules) are on opposite sides of the double bond.
  • cis-2-bromocyclopropanecarboxaldehyde demonstrates cis isomerism, where the bromine and the aldehyde group are on the same side of the cyclopropane ring.
The distinction between cis and trans isomers is critical as they often have differing physical and chemical properties, such as melting points and reactivity. Understanding this concept allows students to predict and rationalize the behavior of different isomers in various contexts.

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Most popular questions from this chapter

Explain why hemiacetals, but not full acetals, are formed under basic conditions.

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Provide an argument not involving molecular orbitals to explain why a carbon- oxygen double bond protonates on \(\mathrm{O}\), not \(\mathrm{C}\).

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