Download Nomenclature, Facts, Reactions, Mechanisms and Synthesis | CHEM 3331 and more Exams Organic Chemistry in PDF only on Docsity! A. Nomenclature: (16 points)
Give an acceptable IUPAC name for each of the following compounds. Be sure to indicate the
stereochemistry where appropriate.
R/S
te Iz. 3-Cqe SB) hydony-- cyclapeetfony |) I~ propang]
{- propanal a A gH
2 (LE) 38) = hyloxy |-cyclopenteny| )
7 f) ~ B-meth y/~T-d een - 2S ze HY}
“2ethy/~ 5 -peethy | b=hepten - I-a] 4
Q- eth y|
g weedlary (
6 ~ heptey
(- ol
t %_4
4, H-C =C~CH,CH,CHCH,CH.E =CH 7 :
em c=cctt ai 9 -(-propynyl )~)4-novta gh He 2
5-( propyl)
I, q a Yona divue
B. FACTS: Total = 24 points
1. Label the alkenes as Stable (S) or unstable (U). (6 points)
A Op
Uy
2. Place the alcohols in order of i increasing reactivit
(1=least reactive, 3=most reactive) (6 points)
AES AAR bre
¥ 2 an ald | Sealy dehydration.
| Ze
3. Place the compounds in order of increasing acidity. (1 = weakest acid, 3=strongest)
(6 points)
7
vf
4. Place a'"Y" in the box below any halide that will produce a useful Grignard reagent. -
Place an "N" in the box below any that will not. (6 points)
CHs (rns
Ut
Kl
Xx
oom aYSo™
?
A.
NV
HO <p
N
D. Mechanisms: (12 points )
The reaction below produces a mixture of products. Provide a clear mechanism to explain the formation of
each product. Use curved arrows to indicate "electron flow". Remember to show only one step at a time.
Show all intermediates and all formal charges. Do not show transition states.
—> OH
Sy x * HO | HO
IZ
E, Synthesis: (12 points) fo
Synthesize the molecule below from cyclohexane, any alkenes or alcohols of/three carbons or less, and
any inorganic reagents. (Please do not include mechanisms.)
OH OH
|
( eforcnc
CH2CHy
ae
H, 50, | be at
off
cs : Che Cl CH
CH C He
eae
[then Hog!
eu (
Mg By !
gPy 4
Hee, NCH, CHSC Hs
Chey P Pee
ON Seer)
- Me CR-CHACH, ¢
qs Pe, / J. he. a af 2 HCH
Feras etd
O
|
i. 4 Di. .
Xs Neen A etatHa ct
™ I ree f OU Ctlee
Ty CeHy Wy
Pet He
oa
ia €thern
[ear=aRy
Y-Chtac¢ He Cl
a
6 xs
