Question

Which is the better nucleophile in no solvent, in an aprotic solvent, and a protic solvent?...

Which is the better nucleophile in no solvent, in an aprotic solvent, and a protic solvent? Cl- or Br-

I was under the impression that Cl- was the better nucleophile because it is smaller and can not stabilize the charge as well as Br- thus making it a better nucleophile when in no solvent/ aprotic solvent

I also thought that because the charge is more concentrated in Cl- it was more suscelptible to being protonated in a protic solvent, thus making Br- the better nucleophile in a protic solvent

Please explain why...

Science   Chemistry   
0 0
Add a commentTranscribed image text
Next >

Homework Answers

Answer #1

Bromine is a better nucleophile than Cl(-) in polar protic solvents, but chloride is a better nucleophile than Br(-) in polar aprotic solvents.

This can be explained by three key trends here.

1) nucleophilicity is decreased by hydrogen bonding – and a nucleophile in a protic solvent will be surrounded by solvent molecules it is hydrogen-bonded to. Br- > Cl-

2) hydrogen bonding ability decreases as one goes down a column in the periodic table

3)In polar aprotic or no solvent, in the absence of hydrogen bonding, nucleophilicity increases with basicity.

Cl- > Br-

0 0
Know the answer?
Your Answer:

Post as a guest

Your Name:

What's your source?

Earn Coins

Coins can be redeemed for fabulous gifts.

Log In

Sign Up

Not the answer you're looking for?
Ask your own homework help question
Similar Questions
Which is the better nucleophile in a protic solvent, chloride ion or bromide ion? Try to...
Which is the better nucleophile in a protic solvent, chloride ion or bromide ion? Try to explain this in terms of the nature of the chloride ion and the bromide ion.
Please reply to this post by a classmate. 150 words minimum. I think that a positive...
Please reply to this post by a classmate. 150 words minimum. I think that a positive message is important because it clear the way for positive feedback from your reader or recipient. The positive message conveys information with clarity which determines the way or direction your message is heading. Being able to avoid negative words such as you must, or you should sound like you being forceful and can send the wrong message to the recipient. However, Conveying the right...
Choice question: Which of the following best describes critical theorists’ views on disclosure of social responsibility...
Choice question: Which of the following best describes critical theorists’ views on disclosure of social responsibility information? Corporate social reporting may be beneficial because it gives the impression of concern and change but in fact, will do no more than allow the system to “capture” the radical elements of, for example, socialism, environmentalism or feminism and thus emasculate them. The disclosure of corporate social responsibility information acts to legitimise, and challenge, those providing the information. Greater disclosure of social responsibility...
Provide your responses to each discussion: (Responses were analytical and demonstrated original thought.) Discussion:1 Better fuel...
Provide your responses to each discussion: (Responses were analytical and demonstrated original thought.) Discussion:1 Better fuel economy is the primary motive behind hybridization. The electric cars rely on electricity, then less gasoline or diesel. When the first hybrid cars like Toyota Prius and Honda Insight went on sale in Japan, most automakers felt electric cars couldn’t travel very far on a full charge. In the recent years, electric cars have improved significantly and the sales have been increased too. From...
I have provided the information for the lab below. I want to see the chemical reactions...
I have provided the information for the lab below. I want to see the chemical reactions that take place during each step of the experiment. So in the procedures when a chemical was added i would like to see what the products and byproducts that were formed. I also want to see one over all reaction for this experiment to just get an overview of what exactly is happening during the experiment. Thank you:) Part B: Synthesis of [Co(NH3)5Cl]Cl2 Objective:...
Re word this reflection essay and include more studies on creativity in it. What have I...
Re word this reflection essay and include more studies on creativity in it. What have I Learned? I have learned how to use my brain better, to organize my thinking process in a way to facilitate my perceptions, creativity and innovative thinking methods in a more effective manner. I learned many ideas and findings on how human brain function. For example, according to Tony Buzan, the brain thinks in two ways: association or explosion method. I learned that to change...
You own a large quantity of corn. Today (? = 0), this corn has a certain...
You own a large quantity of corn. Today (? = 0), this corn has a certain grade, or quality, ? 0. The price per bushel of corn is given by ?. As we’ve seen before, revenue is given by price times quantity. Assume the latter to be 1. In practice, because the better the grade, the higher the price you get for corn, we can consider revenue to be simply ??0. Corn might go bad, just like homes or capital...
Which one of the following statements is true? Select one: a. Traditional Keynesian analysis indicates that...
Which one of the following statements is true? Select one: a. Traditional Keynesian analysis indicates that increases in government purchases are a more potent tool than decreases in taxes. b. According to Keynesians, fiscal policy is the first line of defense against economic downturns. c. Advocates of sacrifice ration claim that a zero-inflation target imposes only small costs on society. d. Sacrifice ration implies that a credible commitment to reducing inflation can lower the costs of disinflation by inducing a...
As for the sales forecast for Year 1 through Year 3, these are some important variables...
As for the sales forecast for Year 1 through Year 3, these are some important variables I will go to consider for sales: Economy: The economic condition of the city, the province and the country are variables I need to consider for a sales forecast. If conditions are poor, people will spend less money on consumption. If economic conditions are great, then more people will have extra money to spend. Competition: I need to consider the level of competition I...
Team 5 answer the questions What are 4 key things you learned about the topic from...
Team 5 answer the questions What are 4 key things you learned about the topic from reading their paper? How does the topic relate to you and your current or past job? Critique the paper in terms of the organization and quality. Incentive Systems             In this paper, we will focus primarily on financial rewards that companies use to attract, retain and motivate the brightest and most talented candidates in the labor market. By providing a reward system that...
ADVERTISEMENT
Need Online Homework Help?

Get Answers For Free
Most questions answered within 1 hours.

Ask a Question
ADVERTISEMENT