Draw the structure of an eight-carbon alkene that would yield the following compound (and no others) after treatment with ozone followed by dimethyl sulfide.
The correct answer and explanation is :
To determine the structure of the eight-carbon alkene that, when treated with ozone (O₃) followed by dimethyl sulfide ((CH₃)₂S), yields a single product, follow these steps:
Step 1: Understanding Ozonolysis
Ozonolysis of an alkene involves cleavage of the double bond, forming carbonyl compounds (aldehydes or ketones) depending on the structure of the alkene. When reductive workup is performed using dimethyl sulfide, aldehydes are formed instead of carboxylic acids.
Step 2: Identifying the Product
You haven’t provided the specific ozonolysis product, but the key requirement is that only one product is formed. This suggests that the alkene must be symmetrical, such that both halves of the molecule yield identical carbonyl fragments.
Step 3: Finding an Eight-Carbon Alkene
For an eight-carbon alkene, the simplest symmetrical options include 4-octene and 3,4-dimethyl-2-pentene. However, to ensure a single product, the best candidate is cis- or trans-4-octene.
Step 4: Ozonolysis of 4-Octene
The structure of 4-octene is:
[
CH_3CH_2CH=CHCH_2CH_2CH_3
]
When ozonolysis is performed, the double bond is cleaved, resulting in two butanal (butyraldehyde, CH₃CH₂CH₂CHO) molecules. Since both halves of the alkene are identical, only one type of product forms.
Final Answer: The Correct Alkene
The correct structure of the starting alkene is 4-octene (CH₃CH₂CH=CHCH₂CH₂CH₃). This structure ensures that ozonolysis produces only butanal as the sole product.
Would you like a structural diagram of 4-octene as well?