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CHEM 3104 (jJ) Exam 2 Name:^411 ash
Thi~ exam co nt ains 100 po m s from 21 que st ions on 5 pages.
1. (3 points) \Vhich one of th e following compounds is an epoxide?
G.
OCH 3 HO OH
(3 point s) How many as:yrnmetric c arbons are in the structure below?
CI
CI
CI
A. 0 B. 1 f) 2 D. 3 E. 5 F. 7
(3 points) A mixture of two e nantiom ers in e qu ~l amounts is best described by the word A. chiral. D. cliastereorner. C. erythro ~ rac e mi c. E. t hreo.
(:3 point s) :Vhi ch structure represe nt s th e en antiomeT of t he structure on th e left?
CH CH^2 C I 3 H^ CI^ H^ CH (^3) H CI^ "-..../^ H 3C^ ./^ H 3C^ ../^ F^ ./^ H^ ./ "-... (^) C - CI c - CH 3 "-...C -H "-...C -CI "-... C^ '"^ -^ CI^ "-...C^ -H I I^ I^ I^ I^ I C " ." H c ·^ ..,^ CH^3 c·^ ·"^ H^ c··"^ F c ·^ ·"^ H^ c ···..^ CH^ F F / \ F /^ ^ H3C / \ H /^ \ H/^ ^2 H 3C / \ (^) H CH F 3 H^ CH^3 H
(:3 points) H gS O-1 is typically required for adding-\vater to A. conjugated clienes B. cumul ated dienes C"\ illte rnal alkynes ,1). terminal alkyncs V V
(3 point s) Addition of excess hydrogen halide t o an alkyne forms a ~ A. conjug ated cli ene "" B"\ geminal dihalide C. haloalkene D. hal oa lkync E. VI C inal dihalide L
Page 1 of 5 (^) out of 18
----- - ----- ~ - ~-- -~--= --- -~
CHEM 3104 Exam 2
-V
\ ;V hich one of t he following compo unds is the most ac id ic?
C - :J ~ ~
. Cp om s "Which one of the following compo unds is a cumulated cliene'!
."
d 9. ~Chag:::::th~
/..----......
I· ~ H ·~ C00 ~
~
-1'10. (3 points) "Which one of the followin g compounds \vill react the slowest in a Dicls-Aldcr
Give the correct IUPAC name for each compound below.
- (,5 points). hexUlV'\ - ~ i; 01
re action?
o
l
., I
~ r.--
HO -----;..-+-.,1- H
H --.J.^ 1~ -l-,,-+/ -r-- 0 H
Page 2 of ,
6r CHEM 3104 Exam 2
- (5 points). ~
~
S
HBr {t'll)tf~C.
..
~O °c
Give the best answer to each question below.
~ 9. (5 points) Give an examp le of a reaction that is stereospecific reaction that is stereoselective but not ste reospeci fic.
and an example of a
1h
c.
s C;",
r(. r
- ( 5 points) \ IVhy do conjugated dienes undergo both direct and COllj ngate addition?
(A J) /'-/; *V"t be^ COl""^ s;..e^ ~^ r~^ Ii^^0 tI^ ~^ Ce-^ It^ I^ IF^ /^ -I^ he '~(. C(;v")c,,(,G
S
{,., r bo c()o1iQ iJ(' ~ Ie^ :^ Nt ~~~
50 :llll CI-^ (0 -I 'S' eX a.^ ""f^ Ie^ C '" ~d~ CA1- (^) (."r 'n ,)
(j;, (^) c+ r;. ,j) if irtll) (^) ~(" &<. C {baV\ t( (^) ( Cd r1 JIA,~.Je :;; ; ~).
I> out of (^15) Page 4 of 5
CHEM 3104 Exam^2
r (20 point s) Propo se a sy nth esis of tran -:t,4-dime th y lc y doh e xen e (below) from l ,3-but adiene
aud any oth er reagen ts wi t h three or fewer' carbons. Indicat e th e optimal reaction co n
ditions for each of th e reactions involved in th e synthesis, and dr aw th e major produ ct of each s tep of th e synth esis.
1
,
Ife
20 Pa ge 5 of 5 out of 20
