:j: -

LI-IJtt tt

-oil_*A, --

.,. /,,o:Lrl

-#'--A['

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.

OH OH

oAl.)DIBAL-H, he:<ane+

Hso*---------->

(oatalytic amt)u+l.) CH3N4gtsr/eftet-----2.) H3O+3) H2CrO4

o-'pH l-6_

_+ ,:. _.z\g?N:_ __*- .\;z -NHz

a\\o

,/\

lo

+-qPracticeProblems 4tllt20l4 1

[-.. , ,

IrTOA.l of the reactions shown below, draw a structure for the MAJOR organic

I\-_i r ---'--. (l equiv.) |'u#.

'!.f"#

)-'---(:'"' "'":'-:':'i;

exprainthefo,owingequ,ibrium**10""'

I

/

{; *f AA* Keq:062

*'o/-' '

_: As.\= ?,JI

Practice Problems 4l ll 12014

l.) For each of the reactions shown below, draw a structure for the MAJOR organicf-; product.\l (l equiv.)

r.) ,rC.s /H3o+#2.) Raney Ni, H2

ExcessJ{2N-NH2

[,i ,r-\ /),lt{ s1v//Ltt'4

.n

///JrhL M&c*,'*y'r*^ tr

Itr o

\\

(@,*u'+ lltl- \n/\ t t i tt*>

Si!*f--L ' l\,/lc,

ll', r

')ir /\\,/ I /o^N, /*1

11,r

'\--C{,ilo

Chemistr5r 245-&iProblem to accompany lecture

4t9n4

l.) Show how you could prepare the carbonyl compounds shown below usingDibal-H, LiAl(OEt)rH or Grignard reagents:

or(

,,AH

e_.--Jbt-_)

,^UH3C-C:N

ou

,/\

lol; flttt /l*t.b.

7 )Lt'o

o

'-#t'*fr

rt'A\\t/lor'1;#,t \ty'

J\^^f'*

{

^d+}<It/

2.) DMS

l.) CH3MgBr, ether

2.) Give the major organic product for each reaction:

-. Nao

iNHl / CH3CH2OH

e1.) Os, - 78oC

2.) H3O* lHzO .

i\l'vr'f

Chemistry 245-83Problem to accompany lecture

4t7n4

l.) For the structures shown below, give IUPAC names:

o

, 5 - l,so(rc$t - t,? - C\t{o!v,*rx- \t*"r-

1

-t-t

$' rc ' 3- ne\l .- l-oxu AeY'l'> -,et,^il

2-) For the names below, give unambiguous structures:

(3R, 4RFformyl4-methylhex-5-enal

n=

t\ g'/-tl(1&4R}7,7dimethylb icy clol2.2.l I heptan-2-one

lslcVcbnex- I -eneca rbaldehyde

1Y:\2-L

n*t*

l+Wu> w'1- (e^'+'*

Itt*- QrL- w,c{ft,vlo - L Srv, &o-d"

7-o' .)

{/

ractice Problems 4123I 12WTTTIG RXN.

l.) Show how you could make the following alkenes by the Wittig reaction. Theremay be more than one good answer in some cases.

bu

sqtqt

t

v"y =\\,

0

.i'9 -

lt

4'[no') ',t

/i\I

$t ,>'l /u.C {

I$(

o:14=.At\l!.'n'),

+I

u\-"p-0'-^-I

w

N

2.) Explain why the alkyl halide in a Wittig reaction is usually chosen to be a primaryor methyl alkyl halide.

t0

SIrc l( hw &1 /-