Draw the skeletal structure of the indicated species. Marvin JS DC1 Major organic product Note the deuterated hydrogen chloride Help H C N O S F P Marvin JS
The Correct Answer and Explanation is:
It looks like you’re working on an organic chemistry question involving the reaction of a compound with deuterated hydrogen chloride (DCl) and are asked to:
- Draw the skeletal structure of the major organic product using Marvin JS, and
- Explain the reaction and product (in ~300 words).
Since I can’t directly draw with Marvin JS here, I’ll describe the process and give you the explanation. You can then draw the structure in Marvin JS based on this guidance.
Understanding the Reaction:
You’re reacting an organic compound (possibly an alkene or alkyne) with deuterated hydrogen chloride (DCl). This is very similar to a reaction with HCl, but instead of hydrogen (H), you’re adding deuterium (D) — a heavy isotope of hydrogen.
Typical Reaction:
If you start with an alkene (e.g., propene: CH₂=CH–CH₃), and you add DCl, the reaction proceeds via electrophilic addition:
Mechanism:
- The double bond attacks the electrophilic D⁺ (from DCl), forming a carbocation on the more stable carbon (Markovnikov addition).
- The Cl⁻ then quickly attacks the carbocation.
Major Product (Markovnikov):
- The D attaches to the carbon with more H (less substituted).
- The Cl attaches to the carbon that forms the more stable carbocation (more substituted).
For example:
CH₂=CH–CH₃ + DCl → CH₃–CH(Cl)–CH₂D
(Here, deuterium adds to the end carbon, and Cl to the middle one)
Explanation (~300 words):
In this reaction, the addition of deuterated hydrogen chloride (DCl) to an unsaturated hydrocarbon (typically an alkene) proceeds via a classic electrophilic addition mechanism. The alkene’s π electrons act as a nucleophile and attack the electrophilic D⁺ ion. This results in the formation of a carbocation intermediate. According to Markovnikov’s Rule, the D⁺ attaches to the carbon with the greater number of hydrogen atoms (less substituted), while the Cl⁻ attaches to the carbon that can better stabilize the positive charge (more substituted).
This regioselectivity arises because more substituted carbocations are more stable due to hyperconjugation and inductive effects from adjacent alkyl groups. Once the carbocation forms, the chloride ion (Cl⁻) attacks it rapidly to give the final product.
Because the reagent is deuterated, the reaction allows chemists to track where the deuterium ends up, which is useful in mechanistic studies and NMR spectroscopy due to deuterium’s distinct properties.
The final skeletal structure should clearly show:
- The original carbon backbone.
- The added D on the less substituted carbon of the double bond.
- The Cl on the more substituted carbon.
This type of labeling is useful in understanding not just the structure, but also the stereochemistry and regioselectivity of addition reactions.
