Skip to main content
Ch.6 - Alkyl Halides; Nucleophilic Substitution
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728당신이 사용하는 게 아니라요?교과서 변경
모든 교과서Wade 9th EditionCh.6 - Alkyl Halides; Nucleophilic Substitution문제 45c,d
6장, 문제 45c,d

Predict the products of the following SN2 reactions.
(c) Chemical equation illustrating the reaction of sodium thiolate with bromoethane to predict product formation.


(d) Chemical equation showing a substitution reaction with reactants and products for SN2 reactions.

검증된 단계별 안내
1
Step 1: Identify the type of reaction. Both reactions are SN2 reactions, which involve a single-step mechanism where the nucleophile attacks the electrophilic carbon and displaces the leaving group simultaneously.
Step 2: Analyze the reactants in reaction (c). The nucleophile is the phenylthiolate ion (C6H5S⁻), and the electrophile is ethyl bromide (CH3CH2Br). The bromine atom is the leaving group.
Step 3: Predict the product for reaction (c). The phenylthiolate ion will attack the electrophilic carbon in ethyl bromide, forming a new bond between the sulfur atom and the ethyl group. Bromine will be displaced as Br⁻.
Step 4: Analyze the reactants in reaction (d). The nucleophile is the acetylide ion (Na⁺:C≡CH), and the electrophile is a long-chain alkyl chloride (CH3(CH2)8CH2Cl). The chlorine atom is the leaving group.
Step 5: Predict the product for reaction (d). The acetylide ion will attack the electrophilic carbon in the alkyl chloride, forming a new bond between the terminal carbon of the acetylide and the alkyl chain. Chlorine will be displaced as Cl⁻.

비슷한 문제에 대한 검증된 영상 답변:

이 영상 해법은 위 문제에 도움이 된다고 튜터들이 추천한 것입니다.
영상 길이:
5m

주요 개념

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

S<sub>N</sub>2 Mechanism

The S<sub>N</sub>2 mechanism is a type of nucleophilic substitution reaction where a nucleophile attacks an electrophile, resulting in the simultaneous displacement of a leaving group. This reaction occurs in a single concerted step, leading to the inversion of configuration at the carbon center. It is characterized by a bimolecular rate law, meaning the rate depends on the concentration of both the nucleophile and the substrate.
추천 영상:
05:29
Creating Ribonucleosides

Nucleophiles

Nucleophiles are species that donate an electron pair to form a chemical bond in a reaction. In S<sub>N</sub>2 reactions, nucleophiles are typically negatively charged or neutral molecules with lone pairs of electrons. In the given reaction, sodium thiolate (S<sup>-</sup>) acts as the nucleophile, attacking the electrophilic carbon in bromoethane (CH<sub>3</sub>CH<sub>2</sub>Br) to form a new bond.
추천 영상:
08:27
Nucleophilic Addition

Leaving Groups

Leaving groups are atoms or groups that can depart from the substrate during a chemical reaction, taking with them the electrons from the bond they formed with the substrate. A good leaving group is typically stable after departure and can be a halide ion (like Br<sup>-</sup> in this case). The ability of a leaving group to leave easily is crucial for the success of S<sub>N</sub>2 reactions, as it influences the reaction rate and product formation.
추천 영상:
07:22
The 3 important leaving groups to know.
관련 실천
교과서 질문

Draw perspective structures or Fischer projections for the substitution products of the following reactions.

(b)

955
views
교과서 질문

Two of the carbocations in Problem 6-42 are prone to rearrangement. Show how they might rearrange to more stable ­carbocations.

1637
views
교과서 질문

Predict the products of the following SN2 reactions.

(a)

(b)

3155
views
교과서 질문

Using cyclohexane as one of your starting materials, show how you would synthesize the following compounds.

(c)

662
views
교과서 질문

Predict the products of the following SN2 reactions.

(e)

(f)

2452
views
교과서 질문

Using cyclohexane as one of your starting materials, show how you would synthesize the following compounds.

(a)

868
views