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Short Answer Questions: Chem223 Practice Exam (Pre Final)

1) The document provides a practice exam for Chem223 with short answer and long answer questions. 2) For short answer questions, students are asked to provide products or reagents for reaction schemes and predict products for multi-step reactions. They are also asked to fill in reaction conditions/products in boxes and suggest a milder method to generate a product. 3) For long answer questions, students are asked to propose synthetic sequences to prepare target molecules from given starting materials, allowing use of main group elements and requiring low carbon reagents. On the final, mechanisms will also be required.

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Jenny Wang
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47 views2 pages

Short Answer Questions: Chem223 Practice Exam (Pre Final)

1) The document provides a practice exam for Chem223 with short answer and long answer questions. 2) For short answer questions, students are asked to provide products or reagents for reaction schemes and predict products for multi-step reactions. They are also asked to fill in reaction conditions/products in boxes and suggest a milder method to generate a product. 3) For long answer questions, students are asked to propose synthetic sequences to prepare target molecules from given starting materials, allowing use of main group elements and requiring low carbon reagents. On the final, mechanisms will also be required.

Uploaded by

Jenny Wang
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
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Chem223 practice exam (pre final)

Short answer questions


Question 1: Give the product(s) or reagents (as required) of the following reactions. Note: transformation
conditions may include more than one reaction.

1) BH3.THF

2) H2O2, NaOH

HBr

peroxide and light

(one step)

Br2, EtOH

CH3

1) Me2CuLi
O
2) H2O

CH2

1) PPh3
2) NaH

Br 3) acetone

HCl

O O
1) NaOEt / EtOH

2) H3O+

1
O O
CN
1) EtMgBr
OH OMe

2) H2O

O O O

O
O O

Ph Me
Me COOPh Ph OH

Question 2:
a) Fill in the boxes
Cat. H2SO4
(conditions or products,
O N C1
as required). H
CN
b) Suggest a milder
method to generate the A B 1) LDA, -78 C

bottom left product C2


2) Ph-CH2Br
from reagent B. C2

Part 3: Long answer questions


Question 1: Propose a synthetic sequence to prepare the following molecule from the starting
material indicated below for each case. Any reagent using inorganic or main group elements (C
excluded) may be used. Note: In this context, PPh3 will be considered a main group element reagent and its
carbon content does not need to be counted.
O OH
a) b) c)

OH

From two molecules of PhCHO and From something with 7 carbon From something with 6 carbon
other reagents with less than two atoms or less (no need to worry atoms or less.
carbon atoms. about alkene stereochemistry)
Note: On the final exam, youll also be asked mechanisms for given reaction (on all the lecture material).

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