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 :
The product of ozonolysis suggests that we need to determine the original structure of the alkene that, upon cleavage, produces only the given product. Here’s how we approach this problem systematically:
Step 1: Understanding Ozonolysis
Ozonolysis of an alkene involves breaking the double bond and replacing it with carbonyl groups. This reaction results in aldehydes or ketones depending on the substitution of the alkene.
Step 2: Identifying the Carbonyl Products
You haven’t provided the exact product structure, but I’ll assume it consists of two carbonyl-containing fragments that originate from an eight-carbon alkene.
- If only a single product is formed, the original alkene must be symmetrical.
- The possible carbonyl compounds could be ketones or aldehydes, and their total carbon count must sum up to 8.
Step 3: Constructing the Possible Alkene
To ensure a single product, the double bond should be positioned symmetrically. A good candidate for such an alkene is 4-octene.
Step 4: Drawing the Structure of 4-Octene
The structure of 4-octene is:
[
CH_3CH_2CH=CHCH_2CH_2CH_3
]
Upon ozonolysis, the C=C bond breaks and is replaced by two identical carbonyl groups, which would yield two molecules of butanal (butyraldehyde):
[
CH_3CH_2CH=CHCH_2CH_2CH_3 \xrightarrow{\text{O}_3/\text{SMe}_2} 2CH_3CH_2CH_2CHO
]
This ensures that only one product is formed, confirming 4-octene is the correct structure.