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Chapter 19: Problem 88

Draw the structural formula for (a) a six-carbon alkane with methyl branches on two adjacent carbons (b) a six-carbon alcohol with an - \(\mathrm{OH}\) group not at the end of the chain (c) a three-carbon organic (carboxylic) acid (d) a four-carbon aldehyde (e) the ester formed when a four-carbon alcohol reacts with a three-carbon acid

Short Answer

Expert verified
The drawings should depict: (a) hexane with methyl branches on two adjacent carbons, (b) a secondary or tertiary hexanol with the -OH group not at the end, (c) propanoic acid with a -COOH group, (d) butanal with a -CHO group on the end, and (e) butyl propanoate formed from the esterification of butanol and propanoic acid.

Step by step solution

01

Drawing a six-carbon alkane with methyl branches

Begin by drawing a linear chain of six carbon atoms to represent the backbone of an alkane. As alkanes have single bonds, connect these carbon atoms with single bonds. Add two methyl groups (-CH3) to two adjacent carbon atoms that are not at the termini of the chain to avoid forming an octane instead of a hexane.
02

Drawing a six-carbon alcohol with an -OH group

Again, start with a linear chain of six carbon atoms. Since we require an -OH group not at the end of the chain, this indicates the alcohol is not a primary alcohol. Choose a carbon that is not the first or last in the chain and add the hydroxyl (-OH) group to it making it a secondary or tertiary alcohol depending on the carbon you choose.
03

Drawing a three-carbon carboxylic acid

Draw a chain of three carbon atoms. At one end of the chain, add a carboxyl group, which is a carbon double-bonded to one oxygen atom and single-bonded to an -OH group. This carboxyl group is depicted as -COOH, making the structure a propanoic acid.
04

Drawing a four-carbon aldehyde

Construct a linear chain of four carbon atoms. On the end of the chain, add a formyl group, which consists of a carbon double-bonded to an oxygen atom and single-bonded to a hydrogen atom, shown as -CHO. This forms butanal, a four-carbon aldehyde.
05

Drawing the ester from the reaction of a four-carbon alcohol with a three-carbon acid

Identify the structures of a four-carbon alcohol (butanol) and a three-carbon acid (propanoic acid) from the previous steps. To form an ester, remove the hydroxyl group from the carboxyl group of the acid and the hydrogen from the -OH group of the alcohol. Combine the remnants to form butyl propanoate, the ester, which includes the alkyl group from the alcohol (butyl-) and the acyl group from the acid (propanoate).

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Key Concepts

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

Structural Formula Representation
Understanding the structural formula of organic molecules is the backbone of organic chemistry education. A structural formula provides a visual representation of an organic molecule, showing how atoms are arranged and connected. It depicts not only the types of atoms but also their connections, which can be single, double, or triple bonds.

For instance, to represent a six-carbon alkane with methyl branches, one would draw a chain of six carbon atoms (hexane) and include two -CH3 groups attached to two adjacent carbons. Such explicit drawings help clarify the molecule's structure, which is crucial when predicting its properties and reactivity.
Alkane Nomenclature
Naming organic molecules, such as alkanes, follows specific rules. Alkanes are hydrocarbons with only single bonds between carbon atoms. The simplest alkanes are named using a prefix that indicates the number of carbon atoms and the suffix '-ane'.

When dealing with branched alkanes, we use the longest carbon chain as the parent name and identify branches or side-chains as substituents using prefixes like 'methyl-' for a one-carbon branch. The carbon chain is numbered to give the lowest possible numbers to the substituents, and the name reflects this ordering.
Alcohol Functional Group
Alcohols are characterized by the hydroxyl group (-OH), which strongly affects the molecule's properties. Due to the polarity of the -OH group, alcohols generally have higher boiling points compared to similar-sized hydrocarbons without an -OH group. Alcohols can be classified as primary, secondary, or tertiary, which indicates the carbon to which the -OH is attached: primary if it’s on an end carbon, secondary if on a middle one with two carbon neighbors, and tertiary if on a carbon connected to three other carbons.
Carboxylic Acid Structure
Carboxylic acids are identified by their carboxyl (-COOH) group, a functional group consisting of a carbon double-bonded to an oxygen (carbonyl group) and single-bonded to a hydroxyl group. This dual functionality impacts their reactivity and makes them acidic. For a three-carbon carboxylic acid, such as propanoic acid, one end of a three-carbon chain will have the carboxyl group. The structure and arrangement confer specific physical and chemical properties to the acids.
Aldehyde Drawing
Aldehydes are another fundamental functional group in organic chemistry, characterized by a carbon atom double-bonded to an oxygen atom and single-bonded to a hydrogen atom — this is known as a formyl group (-CHO). When drawing an aldehyde, one depicts it as a carbon chain with the formyl group at an end carbon atom. In a four-carbon aldehyde such as butanal, the formyl group is attached to the first carbon of the four-carbon chain.
Esterification Reaction
Esterification is a chemical reaction where an alcohol and a carboxylic acid react to form an ester and water. The reaction takes place when the hydroxyl (-OH) group of the carboxylic acid and the hydrogen atom of the alcohol's -OH group are removed, creating water as a byproduct. The remaining oxygen atom from the alcohol forms a bond with the carbon atom of the acid's carbonyl group, resulting in an ester. For example, in butyl propanoate, the ester product of a four-carbon alcohol and a three-carbon acid, the names reflect the combining of 'butyl-' from butanol and 'propanoate' from propanoic acid.

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Most popular questions from this chapter

Draw structural formulas for these esters: (a) \(n\)-nonyl acetate (b) ethyl benzoate` (c) methyl salicylateDraw structural formulas for these esters: (a) \(n\)-nonyl acetate (b) ethyl benzoate (c) methyl salicylate dyan pa si;la

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Which of these compounds are structural isomers of each other? methyl propyl ether, butanoic acid, acetone, propene, 2 -butanol, phenol, methyl propanoate

Draw the structural formulas and write the IUPAC names for all open-chain isomers of (a) pentyne \(\mathrm{C}_{5} \mathrm{H}_{8}\) (b) hexyne, \(\mathrm{C}_{6} \mathrm{H}_{10}\)
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