Scribd
Upload
6 views2 pages

CH 105 - Tutorial 3

The document is a tutorial for CH 105 that includes exercises on chemical transformations, synthesis of molecules, and reaction mechanisms. It requires students to identify products, provide reagents and conditions, and analyze orbital interactions in reactions. Additionally, it poses a question regarding the pathway of solvolysis, asking whether it involves a cation rearrangement or proceeds directly to a product.

Uploaded by

Brian Mackwan
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
6 views2 pages

CH 105 - Tutorial 3

The document is a tutorial for CH 105 that includes exercises on chemical transformations, synthesis of molecules, and reaction mechanisms. It requires students to identify products, provide reagents and conditions, and analyze orbital interactions in reactions. Additionally, it poses a question regarding the pathway of solvolysis, asking whether it involves a cation rearrangement or proceeds directly to a product.

Uploaded by

Brian Mackwan
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
You are on page 1/ 2

CH 105 - Tutorial 3

1. Write the products for the following transformations. Clearly mention the stereochemistry of the
products.
a. b.
Δ Δ
hv A B
A + B O O
O O O O

c. d.
OMe
Δ
-10 oC 20 oC +
A B CHO

2. Give appropriate reagents, reaction conditions and starting materials (if not provided) to synthesize
the following molecules.
a. b.
OH
O
CO2Me

OH CO2Me
3. The reaction given below passes through a five-membered transition state (TS).
Me
+ Me Me
Me
a. Draw the HOMO-LUMO of diene involved.
b. Show both possible combinations of orbital interactions between diene and carbene
(HOMO and LUMO given below) responsible for the product formation.
Me Me
Me Me
LUMO HOMO
(Note: It is an example of cheletropic reaction, which you need not know or remember for solving
this question!).
4. Write a reasonable mechanism for the following reactions. Identify the missing products if any.
Indicate the regio-/stereo-chemistry of the products and reaction intermediates wherever
applicable. Your mechanism should give proper description of the pericyclic processes involved.
a.

b.
O CN
CHO NC CN heat
+ CN
Me NC CN Me CN
CN
5. Does solvolysis proceed via cation 1 followed by rearrangement to 2 (Case 1), or does it proceed
directly to 2 (Case 2)?

(Ref: DePuy, Acc. Chem. Res. 1967, 1, 33)

You might also like