Академический Документы
Профессиональный Документы
Культура Документы
ethynylcyclopropane
Answer:
2.
3,10-dimethyl-6-sec-butylcyclodecyne
Answer:
3.
4-bromo-3,3-dimethyl-1-hexen-5-yne
CH3 Br
Answer: H2C
CH
CH
CH3
4.
acetylene
Answer:
5.
CH3
CH3C
Answer:
CCHCH2CH2CH3
4-methyl-2-heptyne
CH3
6.
Answer:
CH
1-ethynyl-2-methylcyclopentane
59
The compound below has been isolated from the safflower plant. Consider its structure to answer the following
questions.
H
H
C
H3C
C
C
7.
8.
C13H10
We can arrive at the degree of unsaturation for a structure in two ways. Since we know that the
degree of unsaturation is the number of rings and/or multiple bonds in a compound, we can
simply count them. There are three double bonds (3 degrees) and three triple bonds (six
degrees), so the degree of unsaturation is 9.
We can verify this by using the molecular formula, C13H10, to calculate a degree of unsaturation.
The saturated 13-carbon compound should have the base formula C13H28, so (28 - 10) 2 = 18
2 = 9.
9.
H
E C
H3C C
H
C E
C C
H
60
1,4-pentadiene
12. Show the energy differences between the hydrogenation of 1,4-pentadiene and 1-pentyne on a reaction
energy diagram.
Answer:
A = 1-pentyne
B = 1,4-pendatiene
C = 1-pentene
D = pentane
A
Energy
B
C
292.9 kJ/mol
254.4 kJ/mol
D
Reaction Progress
A saturated four carbon compound has the formula C4 H10 . Therefore this compound has
(10 6) 2 = 2 degrees of unsaturation.
14. Draw six of the nine possible structures with this formula.
Answer:
H
H2C
CCH2CH3
C
CH3C
CCH3
H2C
CHCH
CH2
CHCH3
CH3
CH3
CH2
Predict the product of each reaction below. Be sure to indicate stereochemistry when appropriate.
Br
15.
2 KOH
ethanol
Br
61
Answer:
Br
2 KOH
ethanol
Br
16.
CH3CH2
D2
CH3
Lindlar catalyst
Answer:
CH3CH2
D2
CH3
CH3CH2
CH3
C
Lindlar catalyst
17.
1. BH3, THF
2. H2O2, NaOH, H2O
C
D
Answer:
O
18.
1. BH3, THF
2. H2O2, NaOH, H2O
1. NaNH2, NH3
2. CH3CH2I
1. NaNH2, NH3
2. CH3CH2I
CH2
Answer:
C
CH2CH3
KMnO4
19.
H3O+
Answer:
KMnO4
+
H3O
62
COOH
COOH
Chapter 8: Alkynes: An Introduction to Organic Synthesis
20.
CH3CH2C
CH
HgSO4, H2SO4
H2O
Answer:
O
CH3CH2C
CH
HgSO4, H2SO4
H2O
CH3CH2CCH3
CH
CH
CH
CH
excess H2
Pd/C
21.
Answer:
CH2CH2CH2CH3
excess H2
Pd/C
HBr
CH3COOH
CH3CH2CH2CH2
CH2
22. On the structures provided, draw arrows showing the electron flow for the reaction mechanism for the
electrophilic addition of hydrogen bromide to 1-hexyne
CH3CH2CH2CH2
Br
+
C
CH3CH2CH2CH2
CH2
Br
Br
CH3CH2CH2CH2
CH2
Answer:
CH3CH2CH2CH2
Br
CH3CH2CH2CH2
+
C
CH2
Br
Br
CH3CH2CH2CH2
CH2
63
23. The key intermediate in the electrophilic addition reaction shown above is called:
a.
b.
c.
d.
an acetylenic carbocation
a vinylic bromide
a secondary carbocation
a vinylic carbocation
Answer:
Select the best reagent or sequence of reagents from the list provided which would best accomplish each
transformation below. Place the letter corresponding to the reagent(s) in the blank to the left of each reaction.
Each transformation requires only one answer.
a.
b.
c.
d.
e. 1. Br2, CCl4
2. 2 NaNH2, NH3
f. 1. HCl
2. NaNH2, NH3
g. Li/NH3
h. 1. NaNH2, NH3
2. CH3CH2CH2I
H3C
24.
CH3C
CCH3
H
Answer:
H
C
CH3
g
O
CH2
25.
Answer:
26.
Answer:
64
CH2
CH
CH3
a
C
CH
27.
Answer:
CH
Show all reagents and intermediates necessary to carry out the following conversions.
H
28.
(CH3)2CHCH2C
CH
CH2CH3
C
C
H
(CH3)2CHCH2
Answer:
(CH3)2CHCH2C
CH
1. NaNH2, NH3
2. CH3CH2Br
(CH3)2CHCH2C
CCH2CH3
Li/NH3
CH2CH3
C
(CH3)2CHCH2
OH
29.
CH3CH2C
CH3CH2CHCH2CH2CH3
Answer:
CH3CH2C
1. NaNH2, NH3
2. CH3CH2Br
CH3CH2C
CCH2CH3
H2, Pd/C
or
Li/NH3
CH3CH2CH
CHCH2CH3
1. Hg(OAc)2, H2O,/THF
2. NaBH4
or
1. BH3, THF
2. H2O2, NaOH, H2O
OH
CH3CH2CHCH2CH2CH3
65
Using acetylene and any alkyl halides as starting materials, synthesize the following compounds. More than
one step may be required. Show all reagents and all intermediate compounds in your synthetic scheme.
O
CH3CCH2CH2CH2CH2CH3
30.
2-heptanone
(responsible for the odor of cheddar cheese)
Answer:
HC
1. NaNH2, NH3
CH
2. CH3CH2CH2CH2CH2I
HC
CCH2CH2CH2CH2CH3
HgSO4, H2SO4
H2O
O
CH3CCH2CH2CH2CH2CH3
31.
Answer:
HC
1. NaNH2, NH3
2. C6H5CH2I
CH
CH2C
Cl
32.
Cl
CCH2
CH2C
1. NaNH2, NH3
2. C6H5CH2I
CH
Li/NH3
1,2-dichloropropane
(a degreasing solvent used in dry cleaning)
Answer:
HC
CH
1. NaNH2, NH3
2. CH3I
HC
CCH3
H2/Lindlar
or
Li/NH3
H2C
CHCH3
Cl2
CCl4
Cl
Cl
66
33.
O
H3C
OH
acetic acid
(raw material for the vinyl acetate
polymer used in paints and adhesives)
Answer:
HC
CH
1. NaNH2, NH3
2. CH3I
CH3C
CH
1. NaNH2, NH3
2. CH3I
CH3C
CCH3
KMnO4
H3O+
O
2
H3C
OH
Br
34.
CH3CHCH2CH2CH3
Answer:
HC
CH
1. NaNH2, NH3
2. CH3CH2CH2I
HC
CCH2CH2CH3
H2
Lindlar catalyst
H2C
CHCH2CH2CH3
HBr
ether
Br
CH3CHCH2CH2CH3
67