×
Log in to StudySoup
Get Full Access to UCONN - CHEM 2241 - Class Notes - Week 12
Join StudySoup for FREE
Get Full Access to UCONN - CHEM 2241 - Class Notes - Week 12

Already have an account? Login here
×
Reset your password

UCONN / Chemistry / CHEM 2241 / Why is protonating an alcohol reasonable?

Why is protonating an alcohol reasonable?

Why is protonating an alcohol reasonable?

Description

School: University of Connecticut
Department: Chemistry
Course: Organic Chemistry
Professor: Anwar beshir
Term: Fall 2015
Tags: Organic Chemistry, CHEM 2241, Spectroscopy, OH, Ethers, Epoxides, and Organometallic
Cost: 25
Name: CHEM 2241 OH as Leaving Group, Ethers and Epoxides, Organometallics, and Spectroscopy
Description: These notes cover what we learned about making OH a good leaving group and how it participates in chemical reaction, Ethers and Epoxides, Organometallics, and Infrared Spectroscopy. Pages 93-105
Uploaded: 03/29/2016
9 Pages 199 Views 0 Unlocks
Reviews


.lst-kix_7bwo9unjxtj6-0 > li:before{content:"- "}.lst-kix_7bwo9unjxtj6-3 > li:before{content:"- "}.lst-kix_7bwo9unjxtj6-1 > li:before{content:"- "}.lst-kix_7bwo9unjxtj6-2 > li:before{content:"- "}ul.lst-kix_2wp51r4olnys-5{list-style-type:none}ul.lst-kix_2wp51r4olnys-6{list-style-type:none}ul.lst-kix_2wp51r4olnys-3{list-style-type:none}ul.lst-kix_2wp51r4olnys-4{list-style-type:none}ul.lst-kix_2wp51r4olnys-1{list-style-type:none}ul.lst-kix_2wp51r4olnys-2{list-style-type:none}ul.lst-kix_2wp51r4olnys-0{list-style-type:none}ul.lst-kix_2wp51r4olnys-7{list-style-type:none}ul.lst-kix_2wp51r4olnys-8{list-style-type:none}.lst-kix_eeht4qbclcvz-0 > li:before{content:"- "}.lst-kix_eeht4qbclcvz-1 > li:before{content:"- "}.lst-kix_eeht4qbclcvz-3 > li:before{content:"- "}.lst-kix_eeht4qbclcvz-2 > li:before{content:"- "}ul.lst-kix_rod7glxcayjx-8{list-style-type:none}.lst-kix_l25qj6qp86rl-8 > li:before{content:"- "}ul.lst-kix_rod7glxcayjx-7{list-style-type:none}ul.lst-kix_rod7glxcayjx-4{list-style-type:none}.lst-kix_l25qj6qp86rl-7 > li:before{content:"- "}ul.lst-kix_rod7glxcayjx-3{list-style-type:none}ul.lst-kix_rod7glxcayjx-6{list-style-type:none}ul.lst-kix_rod7glxcayjx-5{list-style-type:none}ul.lst-kix_rod7glxcayjx-0{list-style-type:none}.lst-kix_l25qj6qp86rl-4 > li:before{content:"- "}.lst-kix_l25qj6qp86rl-5 > li:before{content:"- "}ul.lst-kix_rod7glxcayjx-2{list-style-type:none}ul.lst-kix_rod7glxcayjx-1{list-style-type:none}.lst-kix_l25qj6qp86rl-6 > li:before{content:"- "}.lst-kix_ijvg3iygnrwq-7 > li:before{content:"- "}.lst-kix_ijvg3iygnrwq-8 > li:before{content:"- "}.lst-kix_ijvg3iygnrwq-4 > li:before{content:"- "}.lst-kix_rod7glxcayjx-0 > li:before{content:"● "}.lst-kix_2wp51r4olnys-8 > li:before{content:"■ "}.lst-kix_ijvg3iygnrwq-5 > li:before{content:"- "}.lst-kix_ijvg3iygnrwq-6 > li:before{content:"- "}.lst-kix_2wp51r4olnys-5 > li:before{content:"■ "}.lst-kix_eeht4qbclcvz-8 > li:before{content:"- "}.lst-kix_2wp51r4olnys-4 > li:before{content:"○ "}.lst-kix_2wp51r4olnys-6 > li:before{content:"● "}.lst-kix_2wp51r4olnys-3 > li:before{content:"● "}.lst-kix_2wp51r4olnys-7 > li:before{content:"○ "}ul.lst-kix_eeht4qbclcvz-0{list-style-type:none}ul.lst-kix_eeht4qbclcvz-1{list-style-type:none}.lst-kix_eeht4qbclcvz-7 > li:before{content:"- "}ul.lst-kix_eeht4qbclcvz-2{list-style-type:none}ul.lst-kix_eeht4qbclcvz-3{list-style-type:none}ul.lst-kix_eeht4qbclcvz-4{list-style-type:none}.lst-kix_eeht4qbclcvz-4 > li:before{content:"- "}.lst-kix_eeht4qbclcvz-5 > li:before{content:"- "}ul.lst-kix_eeht4qbclcvz-5{list-style-type:none}ul.lst-kix_eeht4qbclcvz-6{list-style-type:none}ul.lst-kix_eeht4qbclcvz-7{list-style-type:none}ul.lst-kix_eeht4qbclcvz-8{list-style-type:none}.lst-kix_eeht4qbclcvz-6 > li:before{content:"- "}.lst-kix_rod7glxcayjx-8 > li:before{content:"■ "}.lst-kix_2wp51r4olnys-1 > li:before{content:"○ "}.lst-kix_rod7glxcayjx-7 > li:before{content:"○ "}.lst-kix_2wp51r4olnys-0 > li:before{content:"● "}.lst-kix_2wp51r4olnys-2 > li:before{content:"■ "}.lst-kix_rod7glxcayjx-6 > li:before{content:"● "}.lst-kix_rod7glxcayjx-3 > li:before{content:"● "}ul.lst-kix_7bwo9unjxtj6-6{list-style-type:none}.lst-kix_rod7glxcayjx-5 > li:before{content:"■ "}ul.lst-kix_7bwo9unjxtj6-7{list-style-type:none}.lst-kix_rod7glxcayjx-1 > li:before{content:"○ "}ul.lst-kix_7bwo9unjxtj6-8{list-style-type:none}.lst-kix_rod7glxcayjx-4 > li:before{content:"○ "}ul.lst-kix_7bwo9unjxtj6-2{list-style-type:none}ul.lst-kix_7bwo9unjxtj6-3{list-style-type:none}ul.lst-kix_7bwo9unjxtj6-4{list-style-type:none}ul.lst-kix_7bwo9unjxtj6-5{list-style-type:none}ul.lst-kix_7bwo9unjxtj6-0{list-style-type:none}.lst-kix_rod7glxcayjx-2 > li:before{content:"■ "}ul.lst-kix_7bwo9unjxtj6-1{list-style-type:none}.lst-kix_pwz5ukoi072t-2 > li:before{content:"- "}.lst-kix_pwz5ukoi072t-3 > li:before{content:"- "}.lst-kix_pwz5ukoi072t-1 > li:before{content:"- "}.lst-kix_pwz5ukoi072t-5 > li:before{content:"- "}.lst-kix_pwz5ukoi072t-6 > li:before{content:"- "}.lst-kix_pwz5ukoi072t-7 > li:before{content:"- "}ul.lst-kix_owtxnsbsr504-8{list-style-type:none}.lst-kix_pwz5ukoi072t-0 > li:before{content:"- "}.lst-kix_pwz5ukoi072t-8 > li:before{content:"- "}ul.lst-kix_owtxnsbsr504-3{list-style-type:none}ul.lst-kix_owtxnsbsr504-2{list-style-type:none}ul.lst-kix_owtxnsbsr504-1{list-style-type:none}ul.lst-kix_owtxnsbsr504-0{list-style-type:none}ul.lst-kix_owtxnsbsr504-7{list-style-type:none}ul.lst-kix_pwz5ukoi072t-8{list-style-type:none}.lst-kix_owtxnsbsr504-6 > li:before{content:"● "}ul.lst-kix_owtxnsbsr504-6{list-style-type:none}ul.lst-kix_owtxnsbsr504-5{list-style-type:none}ul.lst-kix_pwz5ukoi072t-6{list-style-type:none}ul.lst-kix_owtxnsbsr504-4{list-style-type:none}ul.lst-kix_pwz5ukoi072t-7{list-style-type:none}.lst-kix_owtxnsbsr504-4 > li:before{content:"○ "}.lst-kix_owtxnsbsr504-5 > li:before{content:"■ "}.lst-kix_owtxnsbsr504-3 > li:before{content:"● "}.lst-kix_pwz5ukoi072t-4 > li:before{content:"- "}ul.lst-kix_ijvg3iygnrwq-2{list-style-type:none}.lst-kix_lc6uvc4h7481-0 > li:before{content:"- "}.lst-kix_lc6uvc4h7481-1 > li:before{content:"- "}.lst-kix_owtxnsbsr504-0 > li:before{content:"● "}.lst-kix_owtxnsbsr504-1 > li:before{content:"○ "}ul.lst-kix_ijvg3iygnrwq-1{list-style-type:none}ul.lst-kix_ijvg3iygnrwq-4{list-style-type:none}ul.lst-kix_ijvg3iygnrwq-3{list-style-type:none}.lst-kix_owtxnsbsr504-2 > li:before{content:"■ "}ul.lst-kix_ijvg3iygnrwq-0{list-style-type:none}ul.lst-kix_pwz5ukoi072t-4{list-style-type:none}ul.lst-kix_pwz5ukoi072t-5{list-style-type:none}ul.lst-kix_pwz5ukoi072t-2{list-style-type:none}ul.lst-kix_pwz5ukoi072t-3{list-style-type:none}ul.lst-kix_lc6uvc4h7481-3{list-style-type:none}ul.lst-kix_pwz5ukoi072t-0{list-style-type:none}ul.lst-kix_ijvg3iygnrwq-6{list-style-type:none}ul.lst-kix_lc6uvc4h7481-2{list-style-type:none}ul.lst-kix_pwz5ukoi072t-1{list-style-type:none}ul.lst-kix_ijvg3iygnrwq-5{list-style-type:none}ul.lst-kix_lc6uvc4h7481-1{list-style-type:none}ul.lst-kix_ijvg3iygnrwq-8{list-style-type:none}ul.lst-kix_lc6uvc4h7481-0{list-style-type:none}ul.lst-kix_ijvg3iygnrwq-7{list-style-type:none}ul.lst-kix_lc6uvc4h7481-7{list-style-type:none}ul.lst-kix_l25qj6qp86rl-3{list-style-type:none}ul.lst-kix_lc6uvc4h7481-6{list-style-type:none}.lst-kix_ijvg3iygnrwq-0 > li:before{content:"- "}ul.lst-kix_l25qj6qp86rl-2{list-style-type:none}ul.lst-kix_lc6uvc4h7481-5{list-style-type:none}ul.lst-kix_l25qj6qp86rl-1{list-style-type:none}ul.lst-kix_lc6uvc4h7481-4{list-style-type:none}ul.lst-kix_l25qj6qp86rl-0{list-style-type:none}ul.lst-kix_lc6uvc4h7481-8{list-style-type:none}.lst-kix_ijvg3iygnrwq-3 > li:before{content:"- "}ul.lst-kix_l25qj6qp86rl-8{list-style-type:none}ul.lst-kix_l25qj6qp86rl-7{list-style-type:none}.lst-kix_ijvg3iygnrwq-1 > li:before{content:"- "}.lst-kix_ijvg3iygnrwq-2 > li:before{content:"- "}ul.lst-kix_l25qj6qp86rl-6{list-style-type:none}ul.lst-kix_l25qj6qp86rl-5{list-style-type:none}ul.lst-kix_l25qj6qp86rl-4{list-style-type:none}.lst-kix_853ex4b0x7me-1 > li:before{content:"- "}.lst-kix_853ex4b0x7me-2 > li:before{content:"- "}.lst-kix_l25qj6qp86rl-0 > li:before{content:"- "}.lst-kix_l25qj6qp86rl-1 > li:before{content:"- "}.lst-kix_853ex4b0x7me-3 > li:before{content:"- "}.lst-kix_l25qj6qp86rl-3 > li:before{content:"- "}.lst-kix_853ex4b0x7me-5 > li:before{content:"- "}.lst-kix_853ex4b0x7me-6 > li:before{content:"- "}.lst-kix_853ex4b0x7me-4 > li:before{content:"- "}.lst-kix_l25qj6qp86rl-2 > li:before{content:"- "}.lst-kix_853ex4b0x7me-7 > li:before{content:"- "}.lst-kix_lc6uvc4h7481-2 > li:before{content:"- "}.lst-kix_853ex4b0x7me-8 > li:before{content:"- "}ul.lst-kix_853ex4b0x7me-5{list-style-type:none}ul.lst-kix_853ex4b0x7me-6{list-style-type:none}ul.lst-kix_853ex4b0x7me-7{list-style-type:none}ul.lst-kix_853ex4b0x7me-8{list-style-type:none}ul.lst-kix_853ex4b0x7me-1{list-style-type:none}.lst-kix_lc6uvc4h7481-3 > li:before{content:"- "}ul.lst-kix_853ex4b0x7me-2{list-style-type:none}ul.lst-kix_853ex4b0x7me-3{list-style-type:none}ul.lst-kix_853ex4b0x7me-4{list-style-type:none}.lst-kix_lc6uvc4h7481-4 > li:before{content:"- "}.lst-kix_lc6uvc4h7481-5 > li:before{content:"- "}.lst-kix_lc6uvc4h7481-6 > li:before{content:"- "}.lst-kix_owtxnsbsr504-7 > li:before{content:"○ "}.lst-kix_7bwo9unjxtj6-7 > li:before{content:"- "}.lst-kix_lc6uvc4h7481-8 > li:before{content:"- "}.lst-kix_owtxnsbsr504-8 > li:before{content:"■ "}.lst-kix_lc6uvc4h7481-7 > li:before{content:"- "}.lst-kix_7bwo9unjxtj6-4 > li:before{content:"- "}.lst-kix_7bwo9unjxtj6-8 > li:before{content:"- "}ul.lst-kix_853ex4b0x7me-0{list-style-type:none}.lst-kix_7bwo9unjxtj6-5 > li:before{content:"- "}.lst-kix_853ex4b0x7me-0 > li:before{content:"- "}.lst-kix_7bwo9unjxtj6-6 > li:before{content:"- "}

Making OH a Good Leaving Group

  • OH is a strong base, and therefore is a poor leaving group.
  • One way to make it a good leaving group is to protonate it

        Add to make it , which is a good leaving group.We also discuss several other topics like fzeros matlab

We also discuss several other topics like State the 3 elements of a Romanesque structure.

LG                Conjugate Aid                pKa of Con. Acid

                        15.7 weak acid = strong base = poor LGDon't forget about the age old question of Explain the five sources of power.

                                        -1.7        strong acid = weak base = good LG

Promoting an alcohol is reasonableIf you want to learn more check out What is dynamic bonding?

Don't forget about the age old question of What is Javadoc commenting?

                                                        pKaWe also discuss several other topics like tubuan mask

                                                        -2.5

                                                        -1.7

                        =

Nucleophilic Substitution

Primary Alcohol:

        

  • HI gives H to to protonate it and make it a good leaving group. Then can attack and replace the leaving group

Elimination

  • Adding  will always lead to an elimination reaction

                                

                                        

Elimination reactions prefer to go through a tertiary alcohol because it creates a tertiary carbocation, which is more stable. is preferred. It is easier to dehydrate a tertiary alcohol.

Other alcohol - Activating Reagents

  • Adding to OH makes it a good LG - Brs are d-

Adding Thionyl Chloride  makes it a good LG

Making it into a Sulfonate Ester makes it a good LG

Know these common sulfonyl chloride that can be used to make OH a good LG

The weaker the base, the better the leaving group, and the more reactive it is

Ether and Epoxides

Ether:                                        Epoxide:

Ethers are poor leaving groups. To become a good LG, they must be activated by strain or an acid.

An epoxide is an ether that has been activated by strain. They are good LGs.

Ethers that have been protonated can then be split by either on SN1 or SN2 pathway:

  • Steric Accessibility of nucleophile (SN2)
  • Carbocation stability (SN1)
  • The reaction will go through on the SN1 pathway if a stable carbocation forms.

  • Protonate O with H. The bond breaks before I attacks. By breaking it here instead of the other side of the O a stable carbocation forms a stable carbocation, instead of a primary carbocation. Nu goes to C with more H

Epoxides have a lot of strain because of their shape, which means that they have a high potential energy, and are therefore more ready to react with other molecules. It takes less energy to initiate the reaction. They react to open the ring and release the strain. They react faster than ethers.

When doing a reaction with ethers, first determine if you will be doing SN1 or SN2

  • If breaking a bond to either side of the oxygen would result in the formation of a stable carbocation (tertiary or one with resonance), then do SN1. if both would be methy groups or primary carbocations, then do SN2.
Page Expired
5off
It looks like your free minutes have expired! Lucky for you we have all the content you need, just sign up here