Name:

1. (6 pts) Draw all of the resonance structures for the conjugate base of ethylacetoacetate, starting from the structure provided. Be sure to use arrows to indicate the flow of electrons.

:2

e 0 1 ,v.,,,CCH2CH3 1 I
II
If f )

1 it t'

rz., )

s Cr)L9

., -.i 0 ,
)

0,
1,1
/

1.?

11
)1-/

H H H

-.0 .....-0120.q

z_<-

1,1,3

11

1-1

H -

2. (6 pts) The first step of an aldol reaction is incomplete as shown below. Draw both resonance structures for the enolate ion in the boxes provided. Use arrows to show the movement of all electrons in both the initial reaction and to show how one resonance structure can be converted into the other.

20,29 1,11
H 0 H C C C H I H
I

it

+ HOB

+ F120

Enolate ion
3. (4 pts) The second step of the mechanism involves the attack of this enolate ion another molecule to produce a tetrahedral intermediate. First, draw the lower energy enolate ion resonance structure from above in the box on the left below. Next, complete the mechanism for this step by drawing arrows to show the flow of electrons and draw the structure of the tetrahedral intermediate in the box provided.

H hl
I I II

+ HCCCH
I

0 )
VI

14

H H

c' (

a";

Enolate
4. (2 pts) Fill in the blanks with a word or words that best complete each sentence. The final step of this mechanism is a

Tetrahedral Intermediate

ro

0
Cl

step to give the final product as a

p-hydroxyaldehyde. Usually the reaction continues with a

an a,fl-unsaturated aldehyde and a molecule of water.

elAyd tic,

f t t-1

step to produce

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5. (1 pt each) Draw the major organic product for each of the following reactions. If you think that there is no reaction under the conditions listed, simply write "NR". For any aldol reactions, assume that your initial aldol product dehydrates. For any products that you think will be racemic, simply write "racemic" under the structure.
a) Challenge Question, kind of...

O
CO 2 Et I) NaOF.t / Et01 I 2) 1-130CO2Et

40
c-s ote

b)

Br, / I-10Ae

I) Br, / l'Br3 OH 2) F1,0

d) CH3 H3C C CH3 e) 0

11

C1I),
I, CH3 H20

0
It

NaOH (excess)

1
14,

c1413 I Lc

0
I) Na0Et / Et0H
OEt Br

2) NaOH / H-)0 3) H3 04 / heat

f)

0
NaOH / heat

g)
0

NaOH / heat FI,0

h) 0
I) NaOMe / Nle01-1
OCH3 H 3 CO

2) 1-1 3 0 * (dilute)

Name:

1(cLi
1) LDA
Vt-s

2) C1-13C1-12CH2C1-1,1

j)
I) NaOEt / EtOH OEt 2) I-1 3 0' (dilute)

\fat e

1)c._

k)

I) Na0Et / DOH 2) I-1 3 0+ (dilute)

1)
/ =5

0 2) 3) H304

V ace

m)

3) NH 2NH, / Et0H / A n)
0 /HI C-

tt 0 1-c.
1) LiA1H4 2) H30+
ki"tv.e. Nek0f4

N
CH3

1-11?

IA U

o)

I) LiA1H4
C1-13C1-11CH,CH,

IA 0+1?

t-c Ne,011

C CA
2) H30'

NZ e_t.4..2.,...L6.1 2_

Vs o

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P)
NO2 Fe

/NO L,
pvo
140A w ZJ V te4 _5' 1 1-1 c . HCI / H2O

(\ittai

NaNO 2 / H30+
NH2

0 C 6. (1 pt) Draw the final product of the following sequence of reactions. If you predict the product will be racemic, simply write "racemic" under your structure.

0
OEt

(Role-iw\ Soo Not") I) NaOEt / EtOH (excess),

2) 3) 4) 5) Na011 / H20 SOC12 NaN 3 / A H-,0

1race_

7. (7 pts) Draw the major organic product for each of the following reactions of a diazonium ion.

N?
FIBF4
Cti20 Cu(N0:3 )2 / 1120

6,7 C.---\
K1 1131)02 CuCN

CtiC1

6. Devise an efficient synthesis for the following transformation. More than one step is required. Be sure to draw any stable compound made along the way and to indicate the reagents and conditions necessary to complete each individual step. a) 7 pts
H

CH3 isJ ttO g20

,N) CO3"17'
1-31-15

C)

o y ttua-y,),L).\oc,...F 0 IN
2)
t40 / P7-0
OCY

0 0