Organic Chemistry IFinal Exam ReviewAnswer Key

Multiple Choicela,2d,3d,4c,5d, 6c, 7d, 8a, 9d, l0a, l7b, l2e, l3d, l4a,15a,16a, 17e

Short Answer1. Use the information in the table below to answer the following question.

CH: <+ HH<+HH <+ CHrCHr <+ CH:

I CU1C+ cb Canfic;2. Name the following compound:

CHr <> CHs gaucheConsider the following two compounds:

t r ans - 1,2 -dimethy lcyc lohexane

l, 3 diaxial interactioneclipsedeclipsedeclipsed

3. SkT

3.8 kJ/mol4.0 kJ/mol6.0 kJ/mol

li?iill, @r-t,z'd;ntlrt'clc loAl t e^t

crs- 1,4-dimethylcyclohexane c7clile4urJ- I ,+-urrr ls l r lyruJururrs^drs Cl q rq?x 141Draw the most stable conformation of each molecule. Use the data in the table above to calculate the total strain energy of eachstructure. Indicate which, if either, is more stable, and calculate the energy difference between the two structures.

fra4 - l, Z o(|^ctli I c7 c/ o le x q^e * - /r'/ - d,;, 4 7 /"7.ro Atxa.e

N0 rr erAoLv DE=7.6^3.6

CtJt

ans : 3-(iodomethyl)-2-isopropyl- l-pentanol

3. Compound A, C7H1a, was found to be optically active. On catalytic reduction over a palladium catalyst, one equivalent ofhydrogen gas was absorbed, yielding optically active compound B, C7H16. When compound A was treated with KMnOa in anacidic solution, CO2 bubbled out and compound C was formed. Compound C has the formula C5,H'2O, and it is an opticallyactive ketone. Draw the strucfures of compounds A, B, and C.

Co

-\-- l

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

t-t )

/l

? l r3 4ia* io l5 ' . 2x3,8 =7,6y'5

Reactions

3. trans-2-butene cHclr ' KoH

>

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

-=X #- ry +,-X2. What reagents are required to accomplish the transformation indicate OO"r!{,

I t. OHt,T#F I-,^-- 4 Hro.ptl:- 2-{

"r' ln

/---n l. osoaA\t t ->v'

\--J 2. NaHSo3. H2o

o0Hro4 {. lJ

--;-' \- .r/

Hr! ,n'

Oyzyr;di"e

cH2oH P4.,

-gi le_

I l. Draw all possible products for the following reaction:

NBS, hV

+

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

Cl, >

cH2ct2

Olut€neaf,

5.

l . Hg(OAc)2, H2O/THF

2. NaBH4

5 0CIz

G'ttOH

0tl

11)o:

>2) Zn,H3O-

OO

/\/\)

8b 14 6"et{er

9. Alo"

GN

(9-ccl4

G-

MechanismI . When 3-methylcyclohexene reacts with HCI in ether, one of the products is l-chloro- 1-methylcyclohexane. Show the complete

mechanism for the formation of this product using the curved arrow formalism.

ctlt6+ 6^

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

*ll_, 'c t -

. /J-H

-tlH

-t

Synthesisl. acetylene as your only source ofcarbon

111 > 3-methyl-3-pentanol

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

2. l-bromobutane # l-pentanol

, lp^.*ing *it4 a I qrbo^ cl,vrpeaaet, 'v.akp a 5 ca.Lon,loal"olo)

'Ti alo ,4i5t reacf 61 6"i 'Sna-r/ ReaStnf "r;tA

Fo.-^l{ely/et9'I lna

/\-r/ ')' etle.

\\

frr- \ ^-Yl_u, et/en/\/ tr

l-bromobutane -b 2-hexanol

4r*r/r-, o",'f, J-) 6e^J"h !zoa/t-Urx?r;y,/ &/W u'if| d^ .hil'V"0 t

ft. fiqh-l r r ra l '/\.) '# /\/

ot\ cytLt, etlQ-#7) Hto*

l-bromobutan "

-!--+ 2-methyl-2-hexanol

f "'/h"/h/^/t ,^// /-"''^ a 6n'2"'ntt ry'*Art hi/:-*"o ^i'a o kthd t ya o"7oa'h'4'/'(?_ t?go-, .g

/'.) 9 ,J 2.-

t\ cHolcHrPrAe-€f/^e. z) )1$+

l-butanol ??? > butanal

0

,J

OHI

/\,/

?9

''-)tCl1rc1.

a-,\on

4.

5.

6. l-butanol t ' !

> butanoic acid

Cr 0t

7. cyclohexane cyclohexanone

6.

/ Kn^01\\0,

ute --- )

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

oPt< ., A]u.ci t-J

Crot - \uet f f i^r)

-)tL 0t, acef one

dl

db,

't?1 >

t. tJ ohn).'Hrl/r{F

)

z- ilabr'lto3b'#O

, (.oLlr,,^ ! I

Ic-Hz

fut&_

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

-r)nauQrr",^"/Qugw'- c4'GL6. #. -c14-4LaeQ----n

f-gn, 5{p2 |- f -

"/t&t?tn crJ^,"

Uh-r;b

t/t f %1a*, ke'4, r/,^y'* 'n--]:&44,/

nr/ A, t /

C t7 3c1/z( - c,%_4_l

oH^t /

t t /

t - 'g9-r t<r"?r,r t r /c l ( .

1H7c/lrcct/3 P' Z. l le0F _c+