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Key Final Exam 2040 1516

The document provides instructions for a multi-part organic chemistry problem set. It asks students to: 1) Draw organic products and indicate stereochemistry for several reactions 2) Provide IUPAC names and draw structures for given compounds 3) Analyze steps in a partial synthesis of Trichlorin A and identify reactive sites 4) Compare reaction rates and provide reasoning for choices 5) Propose a mechanism for a pinacol rearrangement 6) Provide reagents for a series of reactions starting with ethylene oxide 7) Synthesize target compounds from given starting materials using necessary reagents 8) Identify most acidic protons, rank acidities, and reactive sites in a given reaction

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142 views8 pages

Key Final Exam 2040 1516

The document provides instructions for a multi-part organic chemistry problem set. It asks students to: 1) Draw organic products and indicate stereochemistry for several reactions 2) Provide IUPAC names and draw structures for given compounds 3) Analyze steps in a partial synthesis of Trichlorin A and identify reactive sites 4) Compare reaction rates and provide reasoning for choices 5) Propose a mechanism for a pinacol rearrangement 6) Provide reagents for a series of reactions starting with ethylene oxide 7) Synthesize target compounds from given starting materials using necessary reagents 8) Identify most acidic protons, rank acidities, and reactive sites in a given reaction

Uploaded by

Anonymous KXjpvM
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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45

1.

k.m^'l'^^s>e.P<^r

^60^^05^

^oH(

Provide the major organic product(s) for the following reactions.


so that stereochemistry

clo^^

Draw the compo

is obvious and indicate i f enantiomers are formed.

enantiomer formation and there is none, you w i l l not receive full credit.

I f yo

Please

carbons as well, you w i l l not receive any credit i f your carbon count is o f f i.e
structure is not correct.

0
H2Cr04, H2O

^ C " <3 /-/

c.
o

M
2.
3 possible products

2.

(2

Provide lUPAC names for the following compound, specifying stereochemistry


necessary.

. )

'

Provide the structure o f the compound corresponding to the following common


name.
Ethylene glycol

1^0

ol-l

m(xny
did
1

i^^s

ioJk

cohAt^orJ

aLttxT
mamas'

Trichlorin A is a natural product with significant toxicity against breast cancer


Some steps in a partial synthesis are shown below.

y^

>

l i ^ ^ " ^
H-

CHjCCH^)/

a.

Circle the two most acidic protons in the starting material.

b.

Provide the reagents A , C, E and the intermediates B and D.

C:

CH2(CH3),C

^ " ^ ^

E:

The dianion B reacts specifically at one o f its nucleophilic sites.

Circle

nucleophilic sites on the and E X P E A I N why the reaction is so

selective

for one site.

li

I %

20
4.

Compare the following sets o f reactions and circle the one that w i l l be faster.
reason for your choice.

NOTE: I f you do not provide the correct reason, or one at

w i l l not receive full credit for your selection.

These are like problems we did i

-oMsrr
2.

DMSO

Reason:

'"^

oA)^'^^a./^

f ClS^^

b.
1.

2.

Rea^om-

5.

Problem

11-55c.

Propose an arrow pushing mechanism for the following reaction.


pinacol rearrangement product.

'7'/)c5^

^10"/

Hint: the third one

Ethylene oxide (oxirane) is a valuable building block for organic synthesis be

carbon o f its two carbon skeleton has a functional group. The key to recognizi

structural unit derived from ethylene oxide is the presence o f Nu-CHj-CH^-OH gr


The following is a series o f reactions starting with ethylene oxide.

Please pr

necessary reagents, A-F, for each conversion.


CI

/
H3C

H3C

CI

H3C

H3C

IX

C:

D:

F:

dec

24
Provide syntheses o f the following compounds using the starting material given
other necessary inorganic and organic reagents.
compounds and you w i l l receive credit for them.
arrow-pushing.

WORK

Hint: the last step is an oxidation.

ll

This is not a mechanism quest

I f you do not know the structure o f cyclohexene or acetyle

may ask for them, but w i l l lose points.

Cyclohexene

Be sure to show all pertinent

BACKWARDS

8.

Many organic reactions can be broadly classified as acid/base reactions,


electrophile/nucleophile.

It is very important do be able to recognize the most

in molecules as well as comparative acidities.


A l l o f the compounds below can react as acids.

a.

Circle the most acidic proton on each compound.

b.

Without using a table, r a n k ^ h e compounds in order o f increasing acidity


the left).

c.

The following reaction is known to occur:

OH

PBn

Br

Identify the Nucleophilic (Nu) and Electrophilic (E) sites i n the starting mater

ea'

of

Br

gp

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