OrganicChemistryI

Final Exam Review

Answer Key
Multiple Choice
l a ,2 d ,3d, 4c , 5d, 6c , 7d , 8 a ,9 d , l 0 a , l 7 b , l 2 e , l 3 d , l 4 a,15a,16a,17e

Short Answer
1. Use the information in the table below to answerthe following question.

l, 3 diaxialinteraction 3.8kJ/mol CH: <+ H H<+H eclipsed 4.0kJ/mol H <+ CHr eclipsed 6.0kJ/mol CHr <+ CH: eclipsed gauche CHr <> CHs Consider the following two compounds: d;ntlrt' tr ans lcyclohexane - 1,2-dimethy cl cl oA l t e^t 1,4-dimethylcyclohexane , + - u r r r l s l r l yr u Ju r u r r s^ d r s crsu rJ- I c7clile4 C l q rq?x 141 Drawthemoststable conformation of each molecule.Usethedatain thetableabove to calculate thetotalstrain energy of each structure.Indicate which, if either,is morestable, andcalculate the energy difference between the two structures.

li?iill, @r-t,z'

4-t,.t-/,k4/-

fra4

- l, Z o(|^ctli I c7c/ole x q^e

- /r'/ - d,;, 4 7/"7.roAtxa.e

N0 rr erAoLv
CtJt

DE=7.6^3.6 t-t )
/l

I CU1C+ cb Canfic; 3.SkT

2. Name the following compound:

lr3 4ia*iol5'. 2x3,8=7,6y

ans: 3-(iodomethyl)-2-isopropyll-pentanol

3.

CompoundA, C7H1a, was found to be optically active. On catalyticreductionover a palladium catalyst,one equivalentof hydrogen gas was absorbed,yielding optically active compound B, C7H16.When compound A was treated with KMnOa in an acidic solution, CO2bubbled out and compound C was formed. Compound C has the formula C5,H'2O, and it is an optically active ketone. Draw the strucfuresof compounds A, B, and C.

C o
-\--

Reactions
l. below: products resulting ,rdf rn" reaction Draw all possible

2.

ry #-=X
I -,^-t. OHt,T#F 4 Hro.ptl:cHclr' KoH > trans-2-butene

+,-X
ln

indicateOO"r!{, to accomplish the transformation arerequired Whatreagents

( ft&e.' met1,7/ 9t;Ft)

I 2-{

"r'

3.

Cl, > cH2ct2

Ol ut
neaf,

l. Hg(OAc)2, H2O/THF

5.

2. NaBH4

/---n
A\tt->

l. osoa
2. NaHSo3. H2o

OH
--;-'

Hro4

G'tto 0
{.

lJ

v'

\--J

\OO

.r/

0tl
1 )o : >
2) Zn,H3O/\/\)

8b
9.

Hr!

6" 14
et{er

O
5 0CIz
yzyr;di"e
P4., gile_ GN

,n'

Alo"

cH2oH

I l. Draw all possibleproductsfor the following reaction: NBS, hV

ccl4

(9-

G-

Mechanism
I. When3-methylcyclohexene reacts with HCI in ether, oneof theproducts is l-chloro1-methylcyclohexane. Showthecomplete mechanism for the formationof this productusingthe curvedarrowformalism.

ctlt
6+ 6^
_,

*ll

./J

-H

-tl
H

-t

'ct-

2.

Show the complete mechanism for the reaction of 2-methyl-2-pentanolwith HBr.

\\

Synthesis
l. acetyleneas your only sourceofcarbon 111 > 3-methyl-3-pentanol

rur/*t /u! {4 h',;V"Bt "

2. l-bromobutane # l-pentanol

,lp^.*ing

*it4

I qrbo^

'Ti

alo ,4i5t reacf 61 6"i 'Sna-r/ ReaStnf t9'

cl,vrpeaaet, 'v.akp a 5 ca.Lon,loal"olo)

"r;tA

Fo.-^l{ely/e

I
/\-r/ '

lna

')

etle.

/\/

frr-

tr

et/en \ ^-Yl_u,

l-bromobutane-b

2-hexanol

4r*r/r-, o",'f, J-) Urx?r;y,/ &/W

6e^J"h !zoa/tu'if| d^ .hil'V"0 t

fiqhl'

/\.)
4.

ft. l

'# /\/
r rr a

o
t\ cytLt, etlQ7 ) Hto *

a 6n'2"'ntt f ry '*Art "'/h"/h/^/t ,^// /-"''^ hi/:-*"o ^i'a o kthd t ya o"7oa'h'4'/' (?_ t?2.go-, .g t\ cHolcHrPrAe9 /'.) ,J
f/^e. z) )1$+
5. l-butanol ??? > butanal

l-bromobutan -!--+ "

2-methyl-2-hexanol

OH

?9
Cl1rc1.

/\,/

''-)t

6.

l-butanol

t'!

> butanoicacid

,J
7. cyclohexane
't?1

Cr 0t
tL 0t,acefone
-)

a-,\on
dl

) \ 0, G /4onq\ C'o>/ tlto*,/aeefo^e i I fitr^.rol)

ut e

---

Kn^01\

> cyclohexanone

6.

o3b ' # O

t.tJ ohn).

'Hrl/r{F
)

z- ilabr'lt

Pt< ., A t-J
]u.ci
Crot

o
\

b, uet ffi^r) -

, (.oLlr,,^ ! I

c-Hz

fut&_

U "/t&t?tn

crJ^,"

h-r;b

g'"Zn-l*/ l^ -/-

-r)nauQrr",^"/ Qugw'c4'GL6. #.
f-gn,

-c14-4LaeQ---'n--]:&44,/

5{p2 - f-

t/t f %1a*,ke'4, r/,^y'*

1H7c/lrcct/3 ' P

tt

t - ' g 9 - r t<r"?r,rtr/cl (.

Z. lle0F

oH C t73c1/z( - c,%_4_ l
nr/

^t/

A,t

_c+