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Organic Chemistry Reactions: Mechanisms and Products, Study notes of Stereochemistry

Moore Norman Technology CenterStereochemistry

A series of organic chemistry reactions with accompanying structures and mechanisms. Students are required to identify the major organic products and propose reasonable mechanisms, including stereochemistry where relevant. Some reactions involve hydride or alkyl shifts.

What you will learn

  • What role do hydride or alkyl shifts play in the rearrangement of intermediates in the given reactions?
  • What are the major organic products for each reaction in the document?
  • What mechanisms account for the formation of each major organic product?

Typology: Study notes

2021/2022

Uploaded on 09/12/2022

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amoda 🇺🇸

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1. (30 pts) Draw the structure for the major organic product(s) of each reaction (one per
box) and specify the most likely mechanism (SN1, SN2, E2, or E1) by which each is
formed. Include stereochemistry where relevant using wedges and dashes. You may write
"+ enantionmer" if a racemic mixture is formed.
a.
b.
""I
111/
OTs
NaI
acetone
Mechanism
DMSO
55°
E2
Mechanism
2
pf3
pf4
pf5
pf8

Partial preview of the text

Download Organic Chemistry Reactions: Mechanisms and Products and more Study notes Stereochemistry in PDF only on Docsity!

  1. (30 pts) Draw the structure for the major organic product(s) of each reaction (one per box) and specify the most likely mechanism (SN1, SN2, E2, or E1) by which each is formed. Include stereochemistry where relevant using wedges and dashes. You may write

"+ enantionmer" if a racemic mixture is formed.

a.

b.

""I 111/ OTs

NaI

acetone

Mechanism

DMSO

E Mechanism

c.

heat

H3C

6 ..

E Mec hanism

Mechanism

d.

CH 3 H3C~ ;-Br H3C

E Mech anism

----- ~~--

  1. (20 pts) Predict the major organic products for each of the following reactions. No arrow-pushing is necessary, though it may help you determine the outcome of the reaction. Be sure to put your final answer in the box (only answers drawn in the box will be graded so feel free to use the remainder of the page as scratch paper).

H

o

pee =

Br

  1. Mg, ether^ OH o
  2. 0

o

O~

  1. (20 pts) Predict the major organic products for each of the following reactions. No arrow-pushing is necessary, though it may help you determine the outcome of the reaction. Be sure to put your final answer in the box (only answers drawn in the box will be graded so feel free to use the remainder of the page as scratch paper).

Br~OH

NaOH,DMSO

~H

-

o ~",,,,,, HCI (dilute), CH^3 CH^2 0H^ ••

I ~H

~H

6. (24 pts) Using reactions discussed in class, identify the best reagents for each

transformation of the following synthesis. More than one step may be involved. Write

your answers in the corresponding blanks at the bottom of the page.

a

-

UOH

d H^ e .- (^) ••

~

~ ~ f ~

c

a. _ d. PCC, CH^2 Cl^2 _

GJ-

1. PhCH 2 MgBr, ether

b (^) .------=---- __PBr3' DMSO e. __ 2. H30+

  1. Mg, ether
  2. CH 20

C .---------------------------3. H30+ f. H-=2'-S_O--"4,'--H--'2:::....0--'-,1_7_0o_C

  1. (12 pts) One Step Retrosynthesis: Propose starting materials containing 6 or fewer carbons (may already contain other functionalization) and any reasonable reagents that might be used to synthesize the following molecules in one step.

Reagents and Solvents

a.

OH

---------7'> 7

Starting Materials

Reagents and Solvents

b.

cr

OH

Starting Materials

There are other acceptable responses!