(Chem 432-G Second Midterm ~ 5 March 2018 —- Professor Grotjahin K On
1. Pick the true statements about the following reaction. Bond dissociation energies in kJ per mole:
CH H474; BreBr 193; H-Br 366; CoHls-Br 346 ki/mol
CH 434
FeBrg catalyst BB 193
C + Br ——> ~~ Cot NS
sue reaction is endothermic C- 8c sie
\e reaction is exothermic H- 137
(C) the activation energy of the reaction is zero Never! 1 £ le) mat"
Dd the first step of the reaction is exothermic =F
ENDS step of the reaction is endothermic Wy CUA , aredivinn fou f
2. Consider the resonance forms
shown for the arenium ion
formed from the bromination of
acetanilide. Which resonance
ak @ A
form contributes most to the
‘overall resonance oe
@ © ey Sates ton
( nun
ams tiny
@IV
(©) All contribute equally. I "
3. In elect
trophilic aromatic substitution, the attacking species (the electrophile) must be:
(a) neutral species.
tively charged species.
acid.
(@ Bronsted-Lowry acid.
(c) carbocation.
4. wate is the chief product of the Friedel-Crafts alkylation of benzene with |-bromobutane and
AIC?
a)-butylbenzene
0) 2-pRenylbutane C Casrtoungewm Cut
(c) 2-methyl-1-phenylpropane
(d) -butylbenzene
(e) 2,2-diphenylbutane - Professor Grotjahn Ke 3
5, Please give correct IUPAC names for the following compounds.
. 0 4,4-ddwety|cycloheptanene
2
3
‘Chem 432-G Second Midterm ~ 5 Mar
(b)
coo §«=— F-chlove -3-mettyl benzaldehyde
Please draw the correct structures of the following compounds.
(c) 7-bromo-1-octyn-4-one ® c
colt ied AAA.
Qo I
@ C-7 , SS
1H, fo
(d) meta-nitrotoluene.
a
BC,
gs + (CHa),NH
so Co7\ O
- Cc’ pn ae le
HN sector, Ut
we Say oe fF
Guts Cs yoy \o- N-CH3
OS WD bry en
Crg-H BM © +H-A
+ WoO! tip +A Chem 432-G Second Midterm $ March 2018 —
9. Propose a reasonable synthesis of the following compounds from the indicated organic starting
material, using any inorganic reagents or organic reagents,
@) - £6
from benze! - OY
yo HIND:
~ gat GS S.
NOL
need to ae fast
w See Sek 1S:06C poe LL. Grades
HON et. mcbea
‘Ch from starting material of your choice
NO2
Riso &
2 oe + some,
Yh — fey “he iy
AN.
CANOE J -
503A
nied, (213 Chem 432-G Second Midterm ~ § March 2018 —- Professor Grotjahn Ke 8
10, Propose a reasonable 5} lowing compounds from the indicated organic starting
material(s), using any inorganic reagents or organic reagents.
(a)
aaa
OY Cam
make -Cl
(e)
1 from benzene and any molecule with 4.carbons or less
one not do Friedel- oe tS ay oes
i yt Ni Nt (OHO
< Alte = ro mah
@ En(g), H<1
from benzaldehyde and any organic
molecules with 3 carbons or less
——ee
ST |
awe
a Aveser me NR oe
Key vor
ZC
i> 16S Loy .
11. Explain the following results, The reaction shown works very well - almost 100% yield within an
hour at room temperature. A similar reaction starting with the I-methylimidazole (i.e. with methy| not
H at position 1) does NOT work. (Note: we learned in Chapter 15 that I2 by itself does not react with
benzene, but does react when nitric acid is added ~ see Extra Point problem at the end of this exam.)
‘Chem 432-G Second Midterm — § March 2018 ~- Professor Grotjlin
(Explain” means use a combination of mechanism, showing arrow-pushing, and words describing
application of basic chemical principles you have learned in general chemistry, 232, and now 432)
H 2h H
wy 2.NaOH as f
lp sclvents = | gs
water and a
ay hic,
2 equiv) —w 2 ( © NN DIBAL-H dilute aq HCI EH ether, -78 °C i? Ow BMH qt CHO i) DO . Cc cat. CH;COOH a0 HN! probably net (i | y © en ga" > = 3 ee E a a + \\ / Eley CHO ae hou Chem 432-G Second Midterm — $ March 2018 — Professor Grotjahn " fo) CH;COOH cat. + NHNH, § ——————> H Wa’ So. 3H H,0, heat Oh Dua 0 H,0, KMn0,, KOH, heat O. f ee }-Cy-no 2 Ce q workupYou might also like
