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The third exam for chem 2320, focusing on multiple choice questions related to compound identification and structures, as well as proposed reactions with their corresponding mechanisms.
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Chem 2320 Exam 3
March 31, 2006
Name: (Please print) (first) (last)
I. Multiple choice questions. (3 points each). Please put your answers on Scantron sheet. Your score will be graded based only on your answers from Scantron sheet.
(a) acetyl acetyl anhydride (b) acetic anhydride (c) ethanyl anhydride (d) ethanoate anhydride (e) None of the above
(a) (E)-N-ethyl-3-pentenamide (b) (Z)-N-ethyl-3-pentenamide (c) (E)-N-ethyl-4-pentenamide (d) (Z)-N-ethyl-4-pentenamide (e) None of the above
(a) N-ethyl-N-methylacetamide (b) N-isoproplacetamide (c) N-ethyl-N-methylpropanmide (d) N-ethyl-N-methylethylamide (e) None of the above
(a) ethyl 4-oxopentanoate (b) ethyl ester methyl ketone (c) ethyl 4-ketonepentanoate (d) ethyl 4-ketone pentyl ester (e) None of the above
H 3 C C O
O (^) O
CH 3
O
NH
C 2 H 5
C N
O
O O
O
O
CH 3
OCH 2 CH 3
CH 3
H 3 CH 2 CO ?
(a) ethanol, NaOH (b) ethanol, H+ (c) methanol, NaOH (d) methanol, H+ (e) None of the above
O
OH
O
OH
(a) (c)
product
(e) none of the above
O
H
(b) (^) OH (^) O O O^ (d)
OH
OH
O
OCH 3
O
OH
OH (a) (^) (b)
OH (c)
O (d)
(e) none of the above
product
O
CH 3
(a) (b) (c) (^) (d)
(e) none of the above
Product
CH 3
OH
CO 2 H
CN
O CH 3
OH
CN
CH 3
OH
CH 2 NH 2
product?
O H
(a) OH
(b) OH
(c) OH
H
H
(d) O OH (e) None of the above
O
OH
(a) (b) (c) (^) (d)
(e) none of the above
OCH 2 CH 3
CH 3
H 3 CH 2 CO
Product
CH 3
O
OCH 2 CH 3
O OCH^2 CH^3
CH 3
O
CH 2 CH 3 H+, removal of water N^ Products H
N N
I
N
II^ III
N N
IV
(a) I, II (b) I, II, IV (c) III, IV (d) II, III (e) None of the above
O (^) 1) reagent (a) CH 3 MgBr
(e) none of the above
O (b) (CH 3 ) 2 CuLi (c) Ph 3 P (d) CH 3 Br H 3 C Ph = C 6 H 5
C
O
H
(a) (^) (b) (c)
(d) (^) (e) none of the above
Product C H 3 C
C H
O
OCH 3
P
O
EtO EtO
C
OH
H C H 3 C
C (^) H C H 3 C
C
O
OCH 3
H
C (^) H C H 3 C
C
O
H
H
C (^) H
H^ C 3 C
C
OH H
H
H
O
OCH 3 H+ removal of water
O
H (^) HS SH
H 2 Raney Ni Product?
O
H O
H
O
OCH 3
II
OCH 3
III
O
OCH 3
H
S S
(a) I (b) II (c) III (d) IV (e) None of the above
O
O O
H C(CH 3 ) 3 Product?
O
O OH
C(CH 3 ) 3
O
O OH
C(CH 3 ) 3 OH OH II III
OH O
H
(a) I (b) II (c) III (d) IV (e) None of the above
III. Propose an electron pushing mechanism for the following reaction. You have to show how to form the hydrazone intermediate. (20 points)
O
H 2 NNH 2 KOH, H 2 O heating
