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Chapter 16: Problem 39

Draw structures for the following compounds: (a) methyl propyl ketone (b) 2-pentanone (c) 2,3 -hexanedione (d) butyrophenone (e) 3-bromo-4-chloro-5-iodo-2-octanone

Short Answer

Expert verified
(a) CH3-CO-CH2-CH2-CH3 (b) CH3-CO-CH2-CH2-CH3 (c) CH3-CO-CH2-CO-CH2-CH3 (d) C6H5-CO-CH2-CH2-CH3 (e) Br-CH2-Cl-CH-I-CH2-CO-CH2-CH3

Step by step solution

01

Understanding the Compound Names

Identify the structural components mentioned in each compound name. For example, prefixes like 'methyl' or 'propyl' denote the types of alkyl groups attached, while suffixes like 'ketone' indicate the presence of a carbonyl group.
02

Drawing Methyl Propyl Ketone

Methyl propyl ketone is a ketone with a methyl group on one side and a propyl group on the other side of the carbonyl group. Draw these two groups attached to the carbonyl (C=O): CH3-CO-CH2-CH2-CH3.
03

Drawing 2-Pentanone

2-Pentanone has a five-carbon chain with a carbonyl group on the second carbon. Draw: CH3-CO-CH2-CH2-CH3.
04

Drawing 2,3-Hexanedione

2,3-Hexanedione has a six-carbon chain with carbonyl groups (C=O) on both the second and third carbon atoms. Draw: CH3-CO-CH2-CO-CH2-CH3.
05

Drawing Butyrophenone

Butyrophenone has a phenyl group (benzene ring, C6H5) attached to the fourth carbon of a butanone chain (four carbons). Draw: C6H5-CO-CH2-CH2-CH3.
06

Drawing 3-Bromo-4-Chloro-5-Iodo-2-Octanone

3-Bromo-4-Chloro-5-Iodo-2-Octanone has an eight-carbon chain with a carbonyl group on the second carbon, bromine on the third carbon, chlorine on the fourth carbon, and iodine on the fifth carbon. Draw: Br-CH2-Cl-CH-I-CH2-CO-CH2-CH3.

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Key Concepts

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

carbonyl group
A carbonyl group is one of the most important functional groups in organic chemistry. It consists of a carbon atom double-bonded to an oxygen atom (C=O). This functional group is highly reactive due to the polarity of the C=O bond. Carbonyl groups are found in a variety of organic compounds, such as aldehydes, ketones, carboxylic acids, and esters.
A carbonyl group in ketones is bonded to two alkyl (or aryl) groups. In aldehydes, one side is bonded to a hydrogen atom and the other side to an alkyl or aryl group.
Understanding the structure of the carbonyl group helps in identifying and drawing various organic compounds.
alkyl groups
Alkyl groups are types of functional groups consisting of only carbon and hydrogen atoms arranged in a chain. They are derived from alkanes by removing one hydrogen atom, which makes them attach to other atoms or groups.
  • Methyl Group (CH3-): The simplest alkyl group consisting of one carbon atom bonded to three hydrogen atoms. An example in naming is 'methyl propyl ketone'.
  • Propyl Group (C3H7-): Formed by removing one hydrogen from propane. An example is 'methyl propyl ketone', where the carbonyl is bonded to a propyl group.
Knowing these groups simplifies the drawing and understanding of organic structures.
functional groups
Functional groups are specific groupings of atoms within molecules that determine the characteristics and chemical reactions of those molecules. Each functional group has distinctive properties. Key functional groups include:
  • Hydroxyl (-OH): Found in alcohols.
  • Carbonyl (C=O): Found in ketones and aldehydes.
  • Carboxyl (-COOH): Found in carboxylic acids.
  • Amine (-NH2): Found in amines.
Recognizing these functional groups is essential for naming and drawing organic compounds.
organic compound nomenclature
Organic compound nomenclature, established by IUPAC, provides a standardized way to name organic chemical compounds. Here are some basic rules:
  • Identify the longest carbon chain in the molecule.
  • Number the chain so that the highest priority functional group gets the lowest possible number.
  • Use prefixes to indicate substituents and their positions on the chain (e.g., 'methyl', 'ethyl').
  • Use suffixes to indicate the main functional group (e.g., 'one' for ketones).
For example, in '2-pentanone', the '2' indicates the position of the carbonyl group, and 'pentanone' indicates a five-carbon chain with a ketone.
substituent groups
Substituent groups are atoms or groups of atoms that replace hydrogen atoms on the parent chain of a hydrocarbon. Examples include halogens (bromo-, chloro-, iodo-), alkyl groups (methyl, ethyl), and others.
  • When drawing compounds, these groups are attached to specific carbons as indicated in the name. For instance, in '3-bromo-4-chloro-5-iodo-2-octanone', bromine, chlorine, and iodine are substituents situated at carbons 3, 4, and 5 respectively.
  • Substituents are named and numbered to minimize confusion and ensure that the structure is understood correctly.
Understanding substituents helps in drawing complex structures accurately.

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Most popular questions from this chapter

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

cis- 1,2 -Cyclopentanediol is much more reactive toward periodic acid than the trans isomer. Explain why.

Treatment of 2-thiabicyclo[2.2.1]heptane (1) with 1 equivalent of hydrogen peroxide affords a mixture of diastereomers 2 and 3 of molecular formula \(\mathrm{C}_{6} \mathrm{H}_{10} \mathrm{OS}\). Both diastereomers 2 and 3 yield the same product \(4\left(\mathrm{C}_{6} \mathrm{H}_{10} \mathrm{O}_{2} \mathrm{~S}\right)\) upon treatment with peracetic acid. Compound 4 is also produced when 1 reacts with 2 equivalents of peracetic acid. Propose structures for compounds \(\mathbf{2}, \mathbf{3}\), and 4. Hint: Start by drawing a good Lewis structure for the starting material \(1 .\)

Draw structures for the following compounds: (a) \((R)-6\)-amino-3-heptanone (b) 5 -fluoropentanal (c) 3-hydroxycyclopentanone (d) phenylacetone (e) \((Z)-4\)-octenal

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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