Skip to main content
Ch.6 - Alkyl Halides; Nucleophilic Substitution
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728당신이 사용하는 게 아니라요?교과서 변경
6장, 문제 47

Strawberry growers have used large quantities of methyl bromide (b.p. 4 °C) to sterilize the soil before planting their crops. Like some of the freons, methyl bromide can diffuse up into the stratosphere, where it damages the protective ozone layer. Agricultural chemists have suggested using methyl iodide (b.p. 43 °C) as a replacement for methyl bromide. Why is methyl iodide likely to be more toxic to agricultural pests (and people) than methyl bromide? Why is methyl iodide less likely to reach the stratosphere than methyl bromide?

검증된 단계별 안내
1
Step 1: Discuss the chemical reactivity of methyl iodide compared to methyl bromide. Methyl iodide contains iodine, which is a larger and more polarizable atom than bromine. This increased polarizability makes methyl iodide more reactive, allowing it to interact more effectively with biological molecules, potentially making it more toxic to pests and humans.
Step 2: Explain the boiling point difference between methyl iodide (43 °C) and methyl bromide (4 °C). The higher boiling point of methyl iodide indicates stronger intermolecular forces, such as van der Waals interactions, due to the larger size and mass of the iodine atom compared to bromine.
Step 3: Relate the boiling point to volatility. Methyl bromide, with its lower boiling point, is more volatile and can more easily evaporate and diffuse into the atmosphere. Methyl iodide, being less volatile, is less likely to reach the stratosphere.
Step 4: Discuss the environmental implications. Methyl bromide's ability to diffuse into the stratosphere contributes to ozone layer depletion. Methyl iodide, due to its reduced volatility, poses a lower risk of atmospheric diffusion and subsequent ozone damage.
Step 5: Highlight the trade-offs. While methyl iodide may be less environmentally damaging in terms of ozone depletion, its increased toxicity requires careful handling and consideration of its impact on human health and ecosystems.

비슷한 문제에 대한 검증된 영상 답변:

이 영상 해법은 위 문제에 도움이 된다고 튜터들이 추천한 것입니다.
영상 길이:
7m

주요 개념

질문에 올바르게 답하기 위해 반드시 이해해야 하는 핵심 개념들은 다음과 같습니다.

Toxicity of Organohalides

Methyl iodide and methyl bromide are both organohalides, but their toxicity can differ due to the nature of the halogen atom. Iodine is generally more electronegative than bromine, leading to stronger interactions with biological systems, which can result in higher toxicity. Additionally, the molecular structure and reactivity of methyl iodide may allow it to disrupt biological processes more effectively than methyl bromide.
추천 영상:
05:11
How to recognize alcohols, amines and ethers.

Volatility and Boiling Points

The boiling point of a compound is a key factor in its volatility, which influences how easily it can evaporate and enter the atmosphere. Methyl bromide has a lower boiling point (4 °C) compared to methyl iodide (43 °C), making it more volatile and likely to escape into the atmosphere. This higher volatility contributes to methyl bromide's greater potential to reach the stratosphere, where it can cause ozone depletion.
추천 영상:
03:08
How IMFs are related to melting and boiling points.

Atmospheric Lifetime and Degradation

The atmospheric lifetime of a compound refers to how long it remains in the atmosphere before being broken down by chemical reactions. Methyl bromide has a longer atmospheric lifetime than methyl iodide, which means it can persist longer and diffuse into the stratosphere. Methyl iodide, being less stable and more reactive, is likely to degrade more quickly in the lower atmosphere, reducing its chances of reaching the stratosphere.
추천 영상:
06:18
Monosaccharides - Ruff Degradation