1. Draw a generic carbocation intermediate, *CR3. 2. What are the R-C-R bond angles in *CR3? 3. What is the shape of *CR3?

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter9: Alkynes: An Introduction To Organic Synthesis
Section9.SE: Something Extra
Problem 55AP
icon
Related questions
icon
Concept explainers
Question

can someone help me solve and understand these strucutres please. i would really appreciate the help.

Supplement to ChemActivity 9, Part A: Bromonium lon
CHE 210
Goal: How do we explain why some electrophilic addition reactions to alkenes produce a mixture of products,
whereas others result only in trans products?
Case #1: HX Addition to an Alkene
Critical Thinking Questions
1. Draw a generic carbocation intermediate, *CR3.
2. What are the R-C-R bond angles in *CR3?
3. What is the shape of *CR3?
4. What is the hybridization of the central carbon atom in *CR3?
5. Which type of hybrid orbitals on the central carbon atom are used to make the C-R bonds?
6. Which orbital is "left over" after the three C-R bonds have been formed? (Hint: This is not a hybrid orbital.)
7. Draw the curved arrows showing movement of electrons for the reaction below (same as the first reaction
in Alkene Mechanism Worksheet 2). In each step, identify the nucleophile (Nu) and the electrophile (E).
(Note: "D" stands for deuterium or "heavy hydrogen". For more information about deuterium, see
ChemActivity 9, Part B, Model 6: Isotopic Labeling, on page 135 of the workbook.)
CI
Hi
D-CI
"cis"
ether
H.
H.
H
D
H
CI
"trans"
8. In one well written sentence, explain how it is possible to end up with both "cis" and "trans" products
shown above.
Transcribed Image Text:Supplement to ChemActivity 9, Part A: Bromonium lon CHE 210 Goal: How do we explain why some electrophilic addition reactions to alkenes produce a mixture of products, whereas others result only in trans products? Case #1: HX Addition to an Alkene Critical Thinking Questions 1. Draw a generic carbocation intermediate, *CR3. 2. What are the R-C-R bond angles in *CR3? 3. What is the shape of *CR3? 4. What is the hybridization of the central carbon atom in *CR3? 5. Which type of hybrid orbitals on the central carbon atom are used to make the C-R bonds? 6. Which orbital is "left over" after the three C-R bonds have been formed? (Hint: This is not a hybrid orbital.) 7. Draw the curved arrows showing movement of electrons for the reaction below (same as the first reaction in Alkene Mechanism Worksheet 2). In each step, identify the nucleophile (Nu) and the electrophile (E). (Note: "D" stands for deuterium or "heavy hydrogen". For more information about deuterium, see ChemActivity 9, Part B, Model 6: Isotopic Labeling, on page 135 of the workbook.) CI Hi D-CI "cis" ether H. H. H D H CI "trans" 8. In one well written sentence, explain how it is possible to end up with both "cis" and "trans" products shown above.
Alkene Mechanism Worksheet 2: Br2 Addition & Halohydrin Formation
CHE 210
Stereochemistry of HX Addition to an Alkene
H
D-CI
"cis"
ether
H.
H
"trans"
Stereochemistry and Regiochemistry of Addition of Brz to an Alkene
H,C
:Br:
Br
:Br
H;C
CH,C,
Br:
H3C
Br
Stereochemistry and Regiochemistry of Halohydrin Formation
H
H
H20
H3C
•C-
-H
H3C
:Br:
CH, Br
Please note that there are two sets of reagents
that will accomplish this transformation:
H,ö:
Br2 / H20
or
NBS / H20 / DMSO
он
H -C-C-
--
CHS Br
CH
dimethyl sulfoxide
(DMSO)
N-bromosuccinimide
(NBS)
A. L. Smith 2021
HI
Transcribed Image Text:Alkene Mechanism Worksheet 2: Br2 Addition & Halohydrin Formation CHE 210 Stereochemistry of HX Addition to an Alkene H D-CI "cis" ether H. H "trans" Stereochemistry and Regiochemistry of Addition of Brz to an Alkene H,C :Br: Br :Br H;C CH,C, Br: H3C Br Stereochemistry and Regiochemistry of Halohydrin Formation H H H20 H3C •C- -H H3C :Br: CH, Br Please note that there are two sets of reagents that will accomplish this transformation: H,ö: Br2 / H20 or NBS / H20 / DMSO он H -C-C- -- CHS Br CH dimethyl sulfoxide (DMSO) N-bromosuccinimide (NBS) A. L. Smith 2021 HI
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 2 images

Blurred answer
Knowledge Booster
Reactive Intermediates
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305080485
Author:
John E. McMurry
Publisher:
Cengage Learning