Organic and natural Chemistry 2 Laboratory

(ABCT357/ABCT3757)

Lab Manual

2014-2015

Shelter Hang Wai, Alston

(alston. [email protected] edu. hk)

Dr . Lee Cheng Hao, Samuel

(chenghao. [email protected] edu. hk)

Organic Biochemistry and biology II Lab (ABCT357, ABCT3757) (Group one) Contact: Alston Lee (alston. [email protected] edu. hk)

Tues 8: 30-11: 30, Clinical: Y1315

Lab supporting ecuries: YK Au / Kan Chan/Arnold

Demonstrators: Dr . Samuel Lee, Alston Lee, Venne Wai Chung, Guo Shuai, Yuen On Ying,

Sep 16 Tue

Acetylation of О±-D-glucopyranose (Expt 1)

Sep 23 Tue

Cis-1, 2, 3, 6-tetrahydro-4, 5-dimethylphthalic anhydride

(Diels-alder reaction) (Expt 2)

Sep 40 Tue

Photochemical Reaction and Acid-catalyzed

Rearrangement: Cycloaddition reactions (Expt. three or more, Part A)

and Jordan Addition (Expt 4, part A)

April 7 Tue

Michael Addition (Expt some, part B)

Oct 14 Tue

Photochemical Reaction and Acid-catalyzed

Rearrangement: Cycloaddition reactions (Expt. several, Part B)

Oct twenty-one Tue

Purification of products and have spectrum to get samples

Organic Chemistry II Laboratory (ABCT357, ABCT3757) (Group two) Get in touch with: Alston Lee (alston. [email protected] edu. hk)

Wednesday 8: 30-11: 30, Laboratory: Y1315

Lab assisting staffs: YK Au / Kan Chan/Arnold

Demonstrators: Alston Lee, Lo Wai Total, Guo Shuai, Yip Yuk Wang Sep 17 Get married

Acetylation of О±-D-glucopyranose (Expt 1)

Sep 24 Get married

Cis-1, 2, 3, 6-tetrahydro-4, 5-dimethylphthalic anhydride

(Diels-alder reaction) (Expt 2)

Oct almost 8 Wed

Photochemical Reaction and Acid-catalyzed

Rearrangement: Cycloaddition reactions (Expt. a few, Part A)

and Michael jordan Addition (Expt 4, part A)

March 15 Get married

Michael Addition (Expt 5, part B)

Oct twenty-two Wed

Photochemical Reaction and Acid-catalyzed

Rearrangement: Cycloaddition reactions (Expt. a few, Part B)

Oct up to 29 Wed

Filter of products and acquire spectrum pertaining to samples

Web page 1 of 8

Expt. 1 . Acetylation of О±-D-glucopyranose

Procedure:

1 . Preheat answer of ZnCl2 in a 50mL pear form flask with air fondre (0. 5 g anhydrous ZnCl2 in 12. your five ml acetic anhydride, this will likely be offered by lab. technician) in normal water bath intended for 10-15 a few minutes.

2 .

Add slowly 2 . 5 g (0. 014 mol) of powdered D-glucose in small portions (roughly in 7-10 portions and 5 minutes for each addition) into the flask.

3.

Swirl the blend gently during the addition to control the energetic reaction and keep swirling to dissolve the powder added..

4.

5.

After addition is completed, heat the flask on a drinking water bath for starters hour. Amazing the content from the flask with cold drinking water, and then put into ice cubes water (120 ml) and stir strenuously to assist the hydrolysis of unreacted acetic anhydride.

6th.

7.

almost 8.

9.

Following 30 minutes, the petrol which 1st separates will gradually firm up. * Collect the elementary product employing Hirsch direct. Record the melting stage. Dissolve the crude merchandise in little amount of hot methanol. Once the elementary product is dissolved, let it cool off and put water to recrystallize it.

10. Filter out the recrystallized product.

14. Record the melting point. (the materials value can be _____ В°C) Question

1 . In this research, О±

О±-D-glucopyranose is obtained. If we make use of

(MeCO)2O/MeCO2Na to react with powdered D-glucose, ОІ

-D-glucopyranose will be resulted. Explain.

~END~

Page two of almost 8

Expt. 2 . Cis-1, 2, 3, 6-tetrahydro-4, 5-dimethylphthalic

anhydride (Diels-alder reaction)

The Diels-Alder reaction is an important, synthetically beneficial reaction in organic biochemistry and biology. It is named after Otto Diels and his student Kurt Alder who were honored the Nobel Prize in chemistry in 1950 in recognition with the importance of their very own discovery. The Diels-Alder reaction is the cycloaddition of a one particular, 3-ПЂ system (a diene) with a ПЂ bond that usually bears a great electronwithdrawing group (a dienophile) to produce a six-membered ring. The reaction is determined (bond breaking and forming occur simultaneously) and therefore brings about high stereoselectivity (products with predictable stereochemistry).

In this...

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