topic 13: i-clicker slides beauchamp 1 nomenclature...
TRANSCRIPT
Topic 13: i-Clicker Slides Beauchamp 1
a. 1,2-diamino-5,11-dioxo-6-isopropoxy-7-hydroxy-9-cyanoundec-3E-en-1-one
b. 3-cyano-5-hydroxy-6-isopropoxy-7,11-dioxo-10,11-diaminoundec-8E-enal
c. 2-amino-5,11-dioxo-6-(2-methylethoxy)-7-hydroxy-9-cyanoundec-3E-enamide
d. 2-(2-oxoethyl)-4-hydroxy-5-(1-methylethoxy)-6,10-dioxo-9,10-diaminodec-3E-enenitrile
e. No entirely correct answer is provided
H
O C
N
O
O
O O
NH2
NH2
H
Nomenclature Question
Q-1:What are the likely reactions of the following carbocation?
C
H3C
CH3
C
H
CH3
a. additionb. eliminationc. rearrangementd. a & b & ce. a & b
Notes: pp 1-5
H
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Topic 13: i-Clicker Slides Beauchamp 2
Q-2:What are the likely reactions of the following carbocation?
Notes: pp 1-5
C
H3C
CH3
C
H
O
a. additionb. eliminationc. rearrangementd. a & be. resonance
H
H
Q-3:What are sites of partial positive polarity?
C
H3C
CH3
C
C
C
C
O
H
H12
34
56
7
H H
H
Notes: pp 1-5
a. 2,3,5b. 2,4,6c. 1,3,5d. 1,2,4,5e. 1,2,4,6
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Topic 13: i-Clicker Slides Beauchamp 3
Q-4:What is the best orbital to receive electronsin and the best orbital to donate electrons from?
Notes: pp 3
σ∗CH
σCH
n2n1
πCO
σCC
σCO
σ∗CC
σ∗CO
π∗CO
donate accept from intoa. πCO π*
CO b. n1 or n2 π*
CO
c. σCO σ*CH
d. σCH σ*CH
e. σCC σ*CH
C
H
HH
C
O
H
MO's of ethanal
Potential Energy
Nuclear Charges
Q5: How many different products can form inthe following reaction (include stereoisomers)?
Notes: p 5
ClD
a. 2b. 4c. 6d. 8e. 10
?
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Topic 13: i-Clicker Slides Beauchamp 4
Q6: Which of the following are isomers, stereoisomers (diastereomers, enantiomers)?
ClD
a. (1,7) (1,2) (3,4)b. (4,5) (1,4) (6,7)c. (3,5) (1,7) (1,2)d. (3,7) (2,3) (7,8)e. There is no answer provided with all parts correct.
D
Cl
H
H
H
H
D
Cl
D
H
H
Cl
H
Cl
D
H
Cl
D
H
H
H
H
Cl
D
H
D
Cl
H
Cl
H
H
D
1 2 3 4
5 6 7 8
isomers (not stereoisomers) diastereomers enantiomers
Only selected answers are provided, not all possible answers.
Notes: pp 5
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Topic 13: i-Clicker Slides Beauchamp 5
Q7: What is a reasonable sequence of steps for a carbonyl reaction in acid?
Notes: pp 4
C
O
CH OH CH3
C
O
CH
O CH3
H
C
O
C
H
C
O
CH
H
O
H3Celimination product
additionproduct
C
O
CH OH CH3
C
O
CH
O CH3
H
C
O
C
H
C
O
CH
H
O
H3Celimination product
additionproduct
C
O
CH O CH3
C
O
CC
O
C
H
C
O
CH
H
O
H3Celimination product
additionproduct
C
O
CH OH CH3
C
O
CH
H
C
O
C
H
C
O
CH
H
O
H3Celimination products
additionproduct
a
b
c
d
e. None of the above is a reasonable carbonyl reaction sequence in acid.
H
O CH3
H
H
O CH3
H
OH CH3
H
H
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Topic 13: i-Clicker Slides Beauchamp 6
Q8: What is a reasonable sequence of steps for a carbonyl reaction in base?
C
O
CH OH CH3
C
O
CO CH3 C
O
C
H
C
O
CH
H
O
H3Celimination product
additionproduct
C
O
CH OH CH3
C
O
CH
H
C
O
C
H
C
O
CH
H
O
H3Celimination product
additionproduct
C
O
CH O CH3
C
O
C
C
O
C
H
C
O
CH
O
H3Celimination product
additionproduct
C
O
CH OH CH3
C
O
CH
H
C
O
C
H
C
O
CH
H
O
H3Celimination products
additionproduct
a
b
c
d
e. None of the above is a reasonable sequence of steps for a carbonyl reaction in base.
O CH3
H
H
O CH3
H
OH CH3
H
H
H
H
O CH3
O CH3
Notes: p 6
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Topic 13: i-Clicker Slides Beauchamp 7
Q9: What is the expected order of reactivity with nucleophiles?
H3C
C
H
O
H3C
C
CH3
O
H3C
C
Cl
O
H3C
C
O
O
H3C
C
N
O
CH3CH3
CH3
1 2 3 4 5
a. 5 > 2 > 4 > 1 > 3
b. 3 > 4 > 1 > 5 > 2
c. 5 > 1 > 2 > 4 > 3
d. 3 > 4 > 2 > 1 > 5
e. The correct answer is not provided.
Notes: pp 7-8
Q10: Which are tautomers of the given structure?
N
O
H
OA 1 2 3
N
O
H
O
N
O
OH
N
O
O H
Possible TautomersComparison Structure
a. only 1
b. only 2
c. only 3
d. 1 and 2
e. 1, 2 and 3
Notes: p 8
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Q11: What are the expected products in the following reaction?
a. only 1
b. only 2
c. only 3
d. only 4
e. only 2 and 3 (racemic mixture)
H3CC
O
H
1. LiAlH42. D3O+ / D2O
CH2
C
O
HD
H3CC
D
O
H
H
H3CC
H
O
D
H
H3CC
H
O
H
D
1 2 3 4
Notes: pp 9-11
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Topic 13: i-Clicker Slides Beauchamp 9
Q12: How do the following reactions compare?
H3CC
O
H
H3CC
O
CH3
H3CC
O
OCH3
AlH3H
Li Na
BH3H
H3CC
O
H
H3CC
O
CH3
H3CC
O
OCH3
AlH3H
Li
AlH3H
Li
Na
BH3H
Na
BH3H
a. All of the reactions work and deliver 1 equivalent of hydride.b. All of the reactions work and reactions 1,2,5 and 6 deliver 1 equivalent of hydride and reactions 3,4,7,8 deliver 2 equivalents of hydride.c. All of the reactions work and reactions 1,2,4,5,6,8 deliver 1 equivalent of hydride and reactions 3 and 7 deliver 2 equivalents of hydride.d. Reactions 1,2,4,5,6 and 8 deliver 1 equivalent of hydride, reaction 3 delivers 2 equivalents of hydride and reaction 7 does not work.e. No answer above is completely correct.
O
AlH3H
Li ONa
BH3H
2. workup
2. workup
2. workup
2. workup2. workup
2. workup
2. workup
2. workup
1
2
3
4
5
6
7
8
Notes: p 12
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Q13: What are the expected products in the following reaction?
a. only 1
b. only 2
c. only 3
d. only 4
e. The correct answer is not shown
1. LiAlD42. H3O+ / H2O
1 2 3 4
H3CC
CH2
O
H3CC
CH2
O
D
H3CC
CH2
O
H
H D
H3CC
CH2
O
D
D
HC
CH2
O
D
H
H HH3C H H
Notes: p 11
Q14: Which PE vs. POR diagram goes with each reaction?Energy Picture 1 Energy Picture 2 Energy Picture 3
A
A*
B
B*
A
A*
B
B*
A
A*
B
B*
Progress of Reaction
Potential Energy
Progress of Reaction Progress of Reaction
Potential Energy
Potential Energy
O
OH
H3O+
H2O
O
O
O
O
H2O
1
2
3
4
OH
H2O
O
H3O+
OH
H2O OH
O
OH
5
6
7
8
OH
H2O
O
HO O
HO OH2
OH
OH H2O
OH3O+
O
H2O
a. PE/POR diagram 1 = (1,2,3,4) / PE/POR diagram 2 = (5,6) / PE/POR diagram 3 = (7,8) b. PE/POR diagram 1 = (1,2,7,8) / PE/POR diagram 2 = (3,4) / PE/POR diagram 3 = (3,4) c. PE/POR diagram 1 = (1,2,5,6) / PE/POR diagram 2 = (3,4) / PE/POR diagram 3 = (7,8) d. PE/POR diagram 1 = (7,8) / PE/POR diagram 2 = (5,6) / PE/POR diagram 3 = (1,2,3,4)
Notes: pp 13-16
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Q15: What is the order of reactivity (1=fastest)?O O
H
a. 3 > 2 > 4 > 1 because of resonance, inductive and steric effects
b. 1 > 3 > 2 > 4 because of resonance and inductive effects
c. 2 > 4 > 1 > 3 because of steric and inductive effects
d. 1 > 3 > 2 > 4 because of steric and resonance effects
e. The correct answer is not shown
1 2 3
1. NaCN2. slow addition of acid
O
4
O
Notes: pp 18-19
cyanohydrins
CR R
O C
NH
Q16: What atom reacts first when laetrile breaks down in acidto form cyanide?
O
O
O
HO
HO
HO
OH
HOHO
OH
O
C
N
a
b
cd
e H-X(acid)
O
H
CH Nlaetrile
hydrogen cyanide
benzaldehyde
sugarH2O
Notes: pp 19-20
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Q17: Match the correct reaction conditions with itsproper reaction?
a. reaction 1 = viii, reaction 2 = v, reaction 3 = vi, reaction 4 = ii, reaction 5 = i
b. reaction 1 = ix, reaction 2 = vi, reaction 3 = v, reaction 4 = ii, reaction 5 = iv
c. reaction 1 = vii, reaction 2 = i, reaction 3 = vi, reaction 4 = iv, reaction 5 = iii
d. reaction 1 = ix, reaction 2 = ii, reaction 3 = v, reaction 4 = iii, reaction 5 = i
e. The correct answer is not shown
1
2
3
4
5OH
O
H
O
OH
1. NaNR22.
1. R2BH2. H2O2 / HO
H2SO4H2O / Hg+2
H2 / Pdquinoline
H2 / Pd Na / NH3
O
O
H
O O1. NaNR22.
1. NaNR22.
1. NaNR22.
i iiiii iv
v vi vii viii ix
3. workup 3. workup3. workup 3. workup
Notes: p 21
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Topic 13: i-Clicker Slides Beauchamp 13
Q18: Identify any mechanistic steps where errors occur?
O
H
H O
H
H
H O H
1
O
HH
2
C
O
HH
C
4
H
H O
H
H
H2C CH
H
HH2C C
H
H
H
7
5
OH
H8
CH2
OH
H O H
H O
H
H
9
C
OH
H
H
H
C
OH
H
H
HC
O
H
H
H
11
H O H
H O
H
H
a. steps 3, 7, 9b. steps 2, 5, 11c. steps 4, 6, 10d. All steps are correcte. The correct answer is not shown
3
6
10
Notes: p 21
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Q-19 How many errors are present in the following mechanism?
Li Li Li LiLi metal
BrR
hexane Li Li Li
BrRLi
BrR
Li
Li Li Li Li Li
Li Br
R
Li
a. 0-1 b. 2-3 c. 4-5 d. 6-7 e. >7
Q-20 How many different R-Br compounds can be made from the following alkanes (in one reaction)?
CH4
a. 6 b. 7 c. 8 d. 9 e. >9
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Q-21 How many different R-Br compounds can be made from the following alkenes (in one reaction)?
a. 6 b. 7 c. 8 d. 9 e. ≥ 10
Q-22 How many different R-Br compounds can be made from the following alcohols (in one reaction)?
H3C OH OH
OH
OH
OHOH
OH
OH
OH
OH
OH
a. 6 b. 7 c. 8 d. 9 e. ≥ 10 C:\Documents and Settings\psbeauchamp.WIN\My Documents\classes\315\i-clicker questions\Topic 13 Carbonyl (C=O) i-Clicker Slides for pdf.doc
Topic 13: i-Clicker Slides Beauchamp 16
Q-23: How many different carbanions can potentially be made from the starting molecules (after an appropriate number of steps)? Include ALL different possibilities.
CH4
a. 9-10 b. 11-12 c. 13-14 d. 15-16 e. ≥ 17
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Q-24: How many bonds represent a reasonable carbonyl (C=O) disconnection strategy?
HCH2C
H H
C
H
O
H
C
H
H2C
H
HC
CH3
CH2
H1
2
3
4
5
6 7
8
9
10
11
12
1314
a. 0 b. 1 c. 3 d. 4 e. ≥ 5
Q-25: How many bonds represent a reasonable epoxide disconnection strategy?
HCH2C
H H
C
H
O
H
C
H
H2C
H
HC
CH3
CH2
H1
2
3
4
5
6 7
8
9
10
11
12
1314
a. 0 b. 1 c. 3 d. 4 e. ≥ 5
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Q-26: How many bonds represent a reasonable R-X / organolithium coupling strategy?
HCH2C
H H
C
H
O
H
C
H
H2C
H
HC
CH3
CH2
H1
2
3
4
5
6 7
8
9
10
11
12
1314
a. 0 b. 1 c. 3 d. 4 e. ≥ 5
Q-27: How many “fatal flaw” steps (wrong steps) are present in the following reaction sequences? Each arrow represents a different synthetic step.
Cl2 / hνCl
1. Li 2.H2C O
OH
CrO3H2O
H
O
Br2
Br
O1. Mg2.
3. workupOH
CrO3pyridine
OH
O
1. BH32. Br2/CH3O
Br1. Mg2. O
3. workup
OH
HBr
Br
1 2 3
4 5 6
78 9
a. 0-1 b. 2-3 c. 4-5 d. 6-7 e. ≥ 8
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Q-28: How many reasonable strategies could be used to make the target molecule (TM)? More than one step can be used.
OH
TM
aldehyde +RBr / Mg
ketone +RBr / Li
ester +LiAlH4
ester +RBr / Mg
aldehyde + alkyne
ketone +alkyne
epoxide +RBr / Mg
epoxide +LiAlH4
SN1 SN2 alkene
?
a. 0-1 b. 2-3 c. 4-5 d. 6-7 e. ≥ 8
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Q-29: How many nitriles below could be prepared using a SN strategy and RX compounds?
H3C C N CN C
N
CN
CN
CN
CN
CN
CN
CN
a. 0-1 b. 2-3 c. 4-5 d. 6-7 e. ≥ 8
Q-30: How many proton transfers are needed to workup the reaction to the indicated products?
CR R
N
OH
H
HC
R R
O
NH
H
H
H
2. workup
intermediate from reaction of nitrile + Grignard
OH H
a. 3 b. 4 c. 5 d. 6 e. ≥ 7
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Q-31: How many errors are in the following mechanism?
H3CCH2
CN
CCH2
CH3
NOH
H
H
2. workupOH HCH3Li
H3CC
CH2
CH3
N
H3C
H
OH
H
H
CCH2
CH3
N
H3C
HH
OH H
CH2C
H3C NH2
CH3
OHHOH
H
CH2C
H3C NH2
CH3
OH
CH2C
H3C NH3
CH3
OH
CH2C
H3C
H3N
CH3
OH
OH2H
CH2C
H3C
CH3
OH
CCH2
CH3
O
H3C
O H
H
OH2H
H2O H
a. 0 b. 1 c. 2 d. 3 e. ≥ 4
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Q-32: Use the same 1st step for all reactions = Mg, and same last step = H3O+/H2O. Only the 2nd step (electrophile) is different in each reaction (shown). How many answers are wrong?
Br
Br
1
2
1 2Possible Products
2. O
H
O
O
OCH3
O
C OO
CH3C N
Br
2.
2.
2.
2.
2.
2.
OH
OH
OH OH
OHHO
OH OH
OH
O
OH
O
OO
a. 3 b. 5 c. 7 d. 11 e. not given
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Q-33: How many starting combinations could lead to a reasonably good yield of the product shown (within 2 steps)?
OH
BrO
Br
Br
O
H
O
O
OH
O
Br
H
O
Br
H2O
11 2 3 4Product
5 6 7
a. 2 b. 3 c. 4 d. 5 e. ≥ 6
Q-34: How many starting combinations could lead to a reasonably good yield of the product shown (within 3 steps)?
OH
Product
Br
and
Br OH
OO
H
O
O
One of these.
a. 3 b. 4 c. 5 d. 6 e. ≥ 7
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Q-35: What would be the most straight forward approach to the following target molecule?
O
TM
*
Br
CH2
OBr
OHH3C OHH3C
*
*
*
aNaCN
bBr
Br
cBr
d. All are similar.e. None are workable.
Q-35: Which oxygen is most likely to react with thionyl chloride, in the mechanism to form an acid chloride?
O
OH S
O
Cl Cl
a
b
O
Cl
SO2 HCl
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Q-37 How many of the following combinations will lead to the indicated target molecule within 2 synthetic steps?
O ? CN
H3C
CN
Br Br
O
H
Br
CH3Br
Br
O
H
Br
1 2 3 4
5 67 8 9
10
Target Molecule
CN
Br
Br
NaCN
a. 1-2 b. 3-4 c. 5-6 d. 7-8 e. 9-10
Q-38 Starting from the given molecules, which approaches could lead to the target molecule?
Target MoleculeOH
* *
a. 1C + 1C + 1C + 1C + 1Cb. 2C + 1C + 1C + 1C c. 3C + 1C + 1C d. 2C + 2C + 1C e. any of the above could work
Starting Molecules: CH4, CH3CH3, CH3CH2CH3, *CH4
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Q-39 How many of the following molecules could be made using a 3C+1C+1Cstrategy?
OH
*
a. 1 b. 2 c. 3 d. 4 e. No correct answer
Starting Molecules: CH4, CH3CH3, CH3CH2CH3, *CH4
OH
*
OH
*OH
*
Target molecules1 2 3 4
Q-40 How many of the following molecules could be made using a 2C+2C+1Cstrategy?
OH
*
a. 1 b. 2 c. 3 d. 4 e. No correct answer
Starting Molecules: CH4, CH3CH3, CH3CH2CH3, *CH4
OH
*
OH
*OH
*
Target molecules1 2 3 4
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Q-41 How many of the following molecules could be made using a 3C+2Cstrategy?
OH
*
a. 1 b. 2 c. 3 d. 4 e. No correct answer
Starting Molecules: CH4, CH3CH3, CH3CH2CH3, *CH4
OH
*
OH
*OH
*
Target molecules1 2 3 4
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Q-42 How many errors are in the given ketalization mechanism, used to protect aldehydes and ketones?
OTsHO
H
HO
RO
H
OH
OH
O
OTs
ketoneOH
OH
HO
OH
O
HO
TsO HOH
O
HO
H
OH
O
HO
H
O
ethylene glycol
HO O
RO
H
O O
ketal
remove H2O
OH H
a. 2-3 b. 3-4 c. 5-6 d. 7-8 e. ≥ 9
C:\Documents and Settings\psbeauchamp.WIN\My Documents\classes\315\i-clicker questions\Topic 13 Carbonyl (C=O) i-Clicker Slides for pdf.doc