Docsity
Docsity

Prepare for your exams
Prepare for your exams

Study with the several resources on Docsity


Earn points to download
Earn points to download

Earn points by helping other students or get them with a premium plan


Guidelines and tips
Guidelines and tips

Organic Chemistry ILLecitation: Instructions for Semester 2 Exam, Lecture notes of Chemistry

Instructions for the Organic Chemistry Semester 2 exam, including rules for taking the exam, points system, and specific questions. It covers topics such as carbocation stability ranking, relative acidity prediction, and reaction mechanisms.

What you will learn

  • Predict the relative acidity of the following O-H containing molecules and explain your answer.
  • Provide a mechanism for the following reaction that explains diastereoselectivity.
  • What is the order of stability for the given carbocations?

Typology: Lecture notes

2021/2022

Uploaded on 09/12/2022

damyen
damyen 🇺🇸

4.4

(27)

274 documents

1 / 10

Toggle sidebar

This page cannot be seen from the preview

Don't miss anything!

bg1
JHt nr S'
\-'
Irall Semester 201-s
0rganic (.hetlistry I
llecitation I trstructtlt' (rlarne, clay) :
lnstnrctiorts
1. Keep the exam closccl Llntil yoLr at'e instrr'tcted to begin.
2. 'l'Ie exant consists of 10 questions. The firstthtngyou shoulcl do is mal<e
sure lhatt lto pagcs are missitlg. lf a page is missit.tg, notify a proctor
imrnecliately
.j. you will have 1l-roup ancl 15 rninules. Qr.restions are labeled from'e;tsy'[r.) tc-r
harci [*x**). Budget yottr titne wisely.
4., Nlal<e sure to show all of yoLrr tvorl<, and this should fit
rlto the space proviclecl. lf you neecl to use the bacl< of the p;iper, you mttst nral<e
nole ol it in the spatcc provided for creclit.
Goocl l,Lr cl<!
1..-(15 PorntsJ
'2.-(20 pointsJ
3.---(12.5 Points)
4.-(1.2.5 pointsJ
5.--[10 points)
6.-(20 pointsl
7.--(10 pointsl
-I[e?.e \l]\rLte ArcuF[Kff
N0{AloRlUr\ 0N lf,L |r'[ir-|I0N
'------ f-I 0['IuL r.t}\]
(J,,i l't,tcirr,'r,-' 1
Ii4 11 f )r--'
qYl" I
f,di -l 4
pf3
pf4
pf5
pf8
pf9
pfa

Partial preview of the text

Download Organic Chemistry ILLecitation: Instructions for Semester 2 Exam and more Lecture notes Chemistry in PDF only on Docsity!

JHt nr^

S'

-'

Irall Semester 201-s 0rganic (.hetlistry^ I

llecitation I^ trstructtlt'^ (rlarne,^ clay)^ :

lnstnrctiorts

1. Keep the^ exam^ closccl^ Llntil^ yoLr^ at'e^ instrr'tcted to^ begin.

  1. 'l'Ie^ exant consists of 10 questions. The^ firstthtngyou^ shoulcl do^ is^ mal<e

sure lhatt lto pagcs^ are missitlg.^ lf^ a^ page is^ missit.tg,^ notify^ a^ proctor

imrnecliately

.j. you^ will have 1l-roup^ ancl^ 15 rninules.^ Qr.restions are labeled^ from'e;tsy'[r.)^ tc-r

harci [x*). Budget yottr^ titne^ wisely.

4., Nlal<e sure^ to show^ all^ of^ yoLrr tvorl<,^ and^ this^ should^ fit

rlto the space^ proviclecl.^ lf you^ neecl^ to^ use^ the^ bacl<^ of the p;iper, you mttst^ nral<e nole ol it in the spatcc^ provided for^ creclit.

Goocl l,Lr cl<!

1..-(15 (^) PorntsJ '2.-(20 (^) pointsJ 3.---(12.5 (^) Points) 4.-(1.2.5 pointsJ 5.--[10 points) 6.-(20 pointsl 7.--(10 pointsl

-I[e?.e \l]\rLte ArcuF[Kff '------^ N0{AloRlUr\ (^) f-I 0['IuL r.t}]0N^ lf,L^ |r'[ir-|I0N

(J,,i l't,tcirr,'r,-' 1

Ii4 11 fqYl" I )r--'

f,di (^) -l 4

1a. Ranl< the foliowing carbocation stability

and brieflJ, explain your^ enswer'. (5 pointsJx

O- O- tl .rd* ,.nOA 3t

from rrosf stable(1) to^ least stable(4)

o

I H^H JL

o

/4^ I

4 oo

Aa^

6-8. *.r-^ &u<osc-J,P\lbll:h^ ts^I (^) -{]q-bocJion" 4.' mr\Ur,^.r- C-ac boc-{ion'/^ bo(dc4^ on^ -h.r?+rc-oni.r-S.*-{^ i.o n lb. Plovidei.tntot'espedticnalleofthcfollowingcalbonylsfeSter',carbdxyffcacitt,

I<ctone, aldehyde, forntalclehyde). 'l'hen^ ranl<^ tirern^ from^ most^ reqctive (1) to^ lecrst

reactive (4)^ (5^ points)*

@ ^'J**{

r) nFl

eslc-c ko\o^r-^ €o.r.^^t^ o._fA

1c. Predict the relative acidity^ of^ tlte following^ O-H^ containing^ molecttles^ ancl

expiain yoLlr^ answer, using stl'rtctrtt'es were possible^ in^ sLlpport,^ (5^ poilrtsJ*.

YOH

\e.-s\

o^ o

& {^3 \

?oH .- () ,z/

rnos+ acl&^ c-^ a*cidi^ c-

Cho t.-36*-o.t.<-<-)

,Gr efi (--> -,1a_ (^ dsora.r-cr-

\d:"o

++ - -\o \A.

vv )^ 9-'*

t-o

Explunation: (^) e .,.o-: (^) ^d&d ce-so,\a,\cc_ (^) S{-b,f,\

'tttl Ao^^

o

name

stability rank

atoL.\tk -_-.'-.

raYo' ?

oa

r<< I

( -!--, ^

ttt_io-o-.aoa (^) S (^) -... (^) , b{ -- (^) I (^) C"..^- cls o (^) clt1oc-,[2-e e^ oLo..2e o rr{o^ o.tL,=f (^) "oC6.^- \r

the

\

, V

2ci. show a^ mechanism^ for^ the follor'ving reaction^ that^ explatns

diastereoselectivity [5 points)x***

n k-l H', (^) X{cu3 PPh HrcJH -- -'>>^ Hsc' bH. {

I I -,P?L,,

Q

6- t/^ 9o 'orrn'il..,tu, (^) \

nu( t,

''^??-

e (^) H n lrr" 6t^

t *]^ r5i cv

o -^ PP- ,lnl / H-l-", Hri

u'

u (^) .,,.u -'-'+,,

H,U'-l:'^,

  1. Show the pt'oductIsJ of the iollowing reactions (^) Ii2,5 point.s^ total,2.5^ poinl-s each) **

a.('l

a"?orr LrAtHo^ '^ (oH

-/ .J

followed by water workup

a-,?o H2SO | | +^ NFt2tt^ --' -_-'- - d**

a\aoH ll=.-> 1 NaH -.' 2. CH3Br

o

6

cfrs

Lr'^ .J ,.-..'r-r , o
fion

gg-!!- (^) (1" - -,2 (^) -

.^--11 H2SO ll\z- (^) cH3oH

5, l'tre 1'ollowing^ two^ alkenes^ coulcl^ theoretically^ be^ converted^ into^ all<ynes^ through

a bromilation/ double^ elirnination^ sequence,^ Which^ one do^ you^ believe^ would^ worl<

better/ faster,^ and explain^ yoLlr^ answer^ using^ stntctures^ to explain yoLtl'elllswer.

[10 points]"xx

A. (^) B"*L,^

I r3v^ r\vl^ Ll 13

r^ st- Ll vr 13

lQrt. (^) vt ^rl

-r,-^

. Nr^Nttl lr3v^ v"J z. l\cll\ll 1. Br H3C (^) ---cH 2. NaNH

which one would work^ better? B.^ u.Jo^ r L,lI l3v r\

PaP

;n$

BP)

-/ B L

H (^) b. rl^ ( tor^ , btL,.
u

u B.

-fl)c+k*rrLrrf 0r c't!^ u^ )s

*0,93t1c.n)o --.> vr1....4^ '^1'uto^ [;_]

H ['lt'P^

'6'frc*r;err)s

.L'

u r nH

"3 -^ -rJz /^
B;f cv'

r'><;

9'rr)

@ ."Js^

{" t)n

@ t"^d)^ +o |l^ 'l br

; sJ^ np^ &'^ 'l;^i*-ho^

$r, .Lic-[^ i^ s

6r"n

P" r-^ -li; '.J fo''"

6. Synthesis Questions. Make sure^ to^ drarv^ out^ allof^ your^ reagetrts^ atid

ir.rtermecliates clearly^ and^ legibly.^ [20 points)**'i

a. (5 points) o tl ,'-,, ol lrr \z\roH

.| c;,+ril

r-rll lo

\N

--=.eou

[)-'.ov

b (5 points) OFI .^^ (^) -- -,-^ /\2/ (, ---^ (,J

'4^w"

Jo,

7, One of the rvarys I<nctwn to^ convert^ l<elones^ into^ eslers^ is^ a^ reacttott^ I<nown as:r

Baeyer-Villiger oxidation. 'l'he^ mechanism^ is^ analogous^ to the^ oxidation^ step of^ the

hydroboration/oxidation leaction.^ Show^ a^ mechanistti^ for^ both^ of^ these reactiotls,

r-rsing the specific re;tctions illustrarted below.****

Oxidation step of^ hydroboration/oxidation^ Baeycr-Vill,ger Oxidalion

ooB H"co-81:l13.U

t-n

o t.l

l-l"C- -oH"

.U nna

n lL/--D_..rn/Vl^ r"l . n

[A] Mechanisrn^ for^ tlte

.), (^ rXoor-- Y-c> H-O-.*r--:>

E\

-o tz

IL3J Mechanism^ for

A

"ffifz

f^ n.c j?o a
cHl

the Baeyer'-Villigcr reactiotr^ [5 points].

^9o*

-*:: -'^ '>

o

H

o^P Flv (=) K ,,O c" cu'')

tl

H.,co- -cH,

oxiclation step oia hydroboration/oxidation [5 lroints).

n/ kO -o[Z ,. I^ At-...-Xr-- (^) ilrc- o

  • f3:'ut\ (^) cH3^ t

-;> ' 'n Acul^ +^

ootz qc"

t rna/l { o,^ $,,o 6Y cn