Chapter 22: Problem 28
Give the structure for each of the following. a. 4 -methyl-1-pentyne b. \(2,3,3\) -trimethyl- 1 -hexene c. 3 -ethyl- 4 -decene
Short Answer
Expert verified
The structures for the given compounds are as follows:
a. 4 -methyl-1-pentyne: \[CH_3C-C\equiv C-CH(CH_3)-CH_3\]
b. 2,3,3 -trimethyl- 1 -hexene: \[CH_2\equiv CH-CH(CH_3)-CH(CH_3)_2-CH_2-CH_3\]
c. 3 -ethyl- 4 -decene: \[CH_3CH_2CH(CH_2CH_3)CH\equiv CHCH_2CH_2CH_2CH_3\]
Step by step solution
01
a. 4 -methyl-1-pentyne
1. Identify the parent chain: For this compound, the parent chain is "pentyne". The "pent" prefix indicates that there are five carbon atoms, while the "yne" suffix indicates that there is a carbon-carbon triple bond.
2. Determine the position of the triple bond: Since the parent chain name has '1-pentyne', the triple bond starts at the carbon-1 (i.e., the first carbon).
3. Add the methyl group: "4-methyl" indicates that there is a methyl group (a single carbon with three hydrogen atoms) attached to the carbon-4 (i.e., the fourth carbon).
4. Combine the components: The structure for 4-methyl-1-pentyne will look like this:
\[CH_3C-C\equiv C-CH(CH_3)-CH_3\]
02
b. 2,3,3 -trimethyl- 1 -hexene
1. Identify the parent chain: The parent chain for this compound is "hexene". The "hex" prefix indicates that there are six carbon atoms, while the "ene" suffix indicates that there is a carbon-carbon double bond.
2. Determine the position of the double bond: Since the parent chain name has '1-hexene', the double bond starts at the carbon-1 (i.e., the first carbon).
3. Add the methyl groups: "2,3,3-trimethyl" indicates that there are three methyl groups attached to carbon-2 and carbon-3 (two methyl groups attached to carbon-3).
4. Combine the components: The structure for 2,3,3-trimethyl-1-hexene will look like this:
\[CH_2\equiv CH-CH(CH_3)-CH(CH_3)_2-CH_2-CH_3\]
03
c. 3 -ethyl- 4 -decene
1. Identify the parent chain: The parent chain for this compound is "decene". The "dec" prefix indicates that there are ten carbon atoms, while the "ene" suffix indicates that there is a carbon-carbon double bond.
2. Determine the position of the double bond: From the name '4-decene', we can see that the double bond starts at the carbon-4 (i.e., the fourth carbon).
3. Add the ethyl group: "3-ethyl" indicates that there is an ethyl group (two carbons with five hydrogen atoms) attached to the carbon-3 (i.e., the third carbon).
4. Combine the components: The structure for 3-ethyl-4-decene will look like the following:
\[CH_3CH_2CH(CH_2CH_3)CH\equiv CHCH_2CH_2CH_2CH_3\]
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
IUPAC Nomenclature
The IUPAC nomenclature system is a standardized method for naming organic chemical compounds. This approach ensures clear and precise communication across different regions and languages. The name of a compound gives insight into its structure and functional groups.
One of the vital principles of IUPAC nomenclature is identifying the **parent chain**, the longest sequence of carbon atoms. The chain typically determines the base name (like "pentane" or "hexene").
Let's go over some key rules of IUPAC naming:
One of the vital principles of IUPAC nomenclature is identifying the **parent chain**, the longest sequence of carbon atoms. The chain typically determines the base name (like "pentane" or "hexene").
Let's go over some key rules of IUPAC naming:
- **Identify the longest chain**: This is essential to find the base name (e.g., "pentyne" in 4-methyl-1-pentyne).
- **Functional groups and indexes**: Examine double or triple bonds in the chain. Use numbers to show where these groups start on the parent chain.
- **Substituents and prefixes**: Identify groups branching off the main chain (e.g., methyl or ethyl). Substituents are named with numbers based on their position.
- **Priority and alphabetical order**: Substituents are arranged alphabetically in some cases, while the priority of functional groups might determine the numbering of the chain.
Alkynes
Alkynes are a class of hydrocarbons containing at least one carbon-carbon triple bond (Cā”C). The suffix "yne" indicates the presence of this bond, distinguishing alkynes from other hydrocarbons. Their general formula is \(C_nH_{2n-2}\).
Key properties of alkynes include:
Key properties of alkynes include:
- **Triple bonds**: These bonds make alkynes more reactive than their single or double-bonded counterparts. The bond is composed of one sigma bond and two pi bonds.
- **Geometry and Hybridization**: Alkynes typically exhibit a linear geometry around the triple bond because of the sp hybridization of the carbon atoms.
- **Nomenclature**: In naming, it's crucial to number the chain to give the lowest possible numbers to the triple bond. The position of the triple bond directly affects the name (e.g., 1-pentyne).
Alkenes
Alkenes contain at least one carbon-carbon double bond and are denoted with the "ene" suffix. The double bond offers distinctive properties and reactivity compared to single-bonded alkanes.
Consider these essential characteristics of alkenes:
Consider these essential characteristics of alkenes:
- **Double bonds**: They consist of one sigma bond and one pi bond, making alkenes more reactive than alkanes.
- **Cis-Trans Isomerism**: This occurs due to the non-rotatable nature of the double bond, leading to different spatial arrangements of groups attached to double-bonded carbons.
- **Naming and numbering**: When naming alkenes, the chain should be numbered to assign the lowest possible number to the double bond, such as in 1-hexene.