:j: - LI-IJ tt tt -o il_ *A, -- .,. / ,,o: Lrl -#'--A[' 2J Synthesis challenge! Devise amethod to make propanal starting from ethyl bromide and any other reagents you think you might need. (HINT: first think of ways to make propanoic acid from ethyl bromide).
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2J Synthesis challenge! Devise amethod to make propanal starting from ethylbromide and any other reagents you think you might need. (HINT: first think ofways to make propanoic acid from ethyl bromide).
gMini-teSt V. Topics: Wittig reaction (chaptd 16), enotate-C
reaction Michael reaction. A{"&,,r-z\4rl/V1.) The following alkenes might be synthesi ,"aAi uffiig reaction, from an appropriate
carbonyl compound and alkyl halide. For each on(, pive'the carbonyl compound and
alkyl halide that you would start with. / \ f r-.. Vl_+^'Dc\A/p --),H
l)/-- ,J$?"
3)0n,/\
tt
\ t\(,-I'--tJ
Ftq
,\N
x'[;2.) In the problem above, one of the products will be diffrcult to prepare in high yield.
Which one, and why witl it be difficult?-\ltur \cia
3.) Use the back of this sheet of paper to complete, stepwise
ht)
4.) Complete the reactions shown below. For the first two, give the MAJOR organicproduct. For the second two, give the missing reagents that would cause thetransformation to occur as shown.
Br
l.) Ph3P:, A2.) n-Buli
5.) Shown below are two products of aldol reactions for each one show how you wouldmake it, starting from the appropriate carbonyl compounds, and using whateverconditions you think would lead to a good yield of the indicated product.
o/W
5,*
Mini-test IV. Topics: aldehyde and ketone nomenclature, synthesis ofaldehydes and ketones, nucleophilic addition reactions at the carbonyl carbon(thus, most of chapter 16).
1.) Provide IUPAC names for the two structures that appear below.
a,a - J:,r,*+r.1 I ,-'()C'+q^-"3,S - d,,,t,a ,
2.) Ozonolysis could be used to generate the diketone shown below from several different
*Tt"t materials. Give two examples of starting material for such a reaction.
In the space below show a complete, stepwise mechanism for the formation of a
hemiacetal of cyclohexanone in acidic ethanol.
f''*{-, U"
or\
o :#,
--
4.) For the first four reactions below, give the major organic product. For the last three,show what reagents/conditions would cause the transformation to occur as shown, byputting them over the reactiorqarrow.
HCN.-------------->
UJ II\H_ ?5','( .o". )
0$
l.) cD3cl, P3h3
--1--r>2.)n-BuLi
l.) DrBAL-H
2.)}I2O--$
- -.- -.
ilo
1 ruh -Nltu
7\) ;-t
tr,e$ e/r
\ffie\
HgSOa /H2SO4
Instructions: For the reactitrc frorn tdtr girc 6e majm organic product.
H3C-C:NHCI(cd.)
-5-
-
H3Ot, A
Chemirnry Dls_ml:0 Reactions Worksheet 2
l.) DrBAL-rr,-7EeC
--L.
.--2.)H2O
,oAo,d*,-o
-,a.- -OCH3 H2SO4' onc droP./ \-z -
-
ll .HrcruoHo
For the reactions shown below, give the missing reagentVconditions over the alrow that would cause thetransformation to occur as shown. Some of the transformations may require more than one step.
Wtr
Lo
.oA"-U t'
---.Lr
--
l.) For the first four reactions, give the major organic product; for the secondfour, show the reagents over the arrow (possibly more than one step) thatwould cause the transformation to occur as shown.
+,+oH-l
.........,'....._
l.)oH-t----+
2.)Heat
+o
&.MCPBA
--------+
MCPBA
----+
4",^.- cH3cH2oH
OH
\,A" -=--+
1.) For the first four reactions, give the major organic product; for the second' four, show the reagents over the arrow (possibly more than one step) that
would cause the transformation to oceur as shown.
o)Uo
,."A,
ry*'
1.) CH3CH2CH2Br, P$3
2.) n-Buli
Hzo
l.) NaNIO2, HCI
2.) CuCN
exctiss CH3OH
m.7-/-N---
oA
XO dda zLtn
1.) For the first four reactions, give the major organic product; for the secondfour, show the reagents over the arrow fuossibly more than one step) thatwould cause the transformation to occur as shown.