Florida Gulf Coast University Organic Chemistry Worksheet

  

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I have attached an example assignment

Module 3 – short answer
1) Provide the major organic product of the following reaction.
2) Provide the major organic product of the following reaction.
3) Provide the major organic product of the following reaction.
4) Provide the balanced equation for the reaction that occurs when bromobenzene is treated with metallic lithium
in hexanes.
5) Provide the structure of the major organic product that results when 1-bromocyclohexene reacts with metallic
magnesium in diethyl ether.
6) Provide the major organic product of the following reactions.
7) Show how the following synthesis could be carried out.
8) How would one use a Grignard-based synthesis to accomplish the following transformation?
benzyl bromide (PhCH2 Br) to 3-phenyl-1-propanol
1
9) Provide the reagents necessary to accomplish the following transformation.
10) What reagents are needed to accomplish the multistep transformation shown below?
11) What reagents are needed to accomplish the multistep transformation shown below?
12) Provide the major organic product of the reaction below.
13) Provide the major organic product of the reaction below.
14) Provide the major organic product of the reaction below.
15) Provide the major organic product of the reaction below.
16) Is an organolithium reagent more reactive than the comparable Grignard reagent or less reactive? Explain
briefly.
17) Complete and balance the following transmetallation reaction.
CH3 CH2 CH2 MgCl + CdCl2
2
18) Complete and balance the following transmetallation reaction.
CH3 CH2 CH2 MgCl + SiCl4
19) Complete and balance the following reaction.
CH3 CH2 CH2 Li + CuI
20) List the sequence of reagents necessary to prepare the appropriate Gilman reagen from ethyl iodide.
21) Provide the major organic product of the reaction below.
22) Provide the major organic product of the reaction below.
23) Provide the major organic product of the following reactions.
24) Provide the major organic product of the following reactions.
3
25) Provide the major organic product of the reaction below.
26) Provide the major organic product of the reaction below.
27) Give the major organic product for the following reaction.
28) Give the major organic product for the following reaction.
29) Provide the major organic product of the reaction below.
30) Provide the major organic product of the reaction below.
4
31) What two-word name is given to a reaction that breaks the carbon-carbon double bond and then rejoins the
fragments with the double bonds forming in a different location?
32) Name the three major aklene products that result when 1-pentene is treated with Grubbs catalyst.
33) Name the organic products that would result from metathesis of 2-methyl-1-pentene.
34) Name the organic products that would result from metathesis of 1,8-nonadiene.
35) Provide the structure of the alkene that will undergo metathesis to generate the compound below.
5
Answer Key
Testname: CH03-SHORT ANSWER
1)
2)
3)
4)
5)
6)
7)
8) 1.
2.
3.
9) 1.
2.
Mg, Et2 O
epoxide (oxirane)
H3 O+
Mg, Et2 O
D2 O
6
Answer Key
Testname: CH03-SHORT ANSWER
10) 1. CH3 CH2 CH2 MgBr
2. H+
11) 1. Mg, ether
2. D2 O
12) CH3 CH3
13) CH3 CH3
14) CH3 CH3
15) CH3 CH3
+
+
CH3 OMgBr
CH3 NHMgBr
CH3 CCMgBr
+
16) R-Li is more reactive. C-Li is more polar than C-Mg because Li is less electronegative than Mg. The carbon atom has
a greater partial negative charge in the organolithium reagent.
17) 2 CH3 CH2 CH2MgCl + CdCl2 (CH3 CH2 CH2)2Cd + 2 MgCl2
18) 4 CH3 CH2 CH2MgCl + SiCl4
(CH3 CH2 CH2)4Si + 4 MgCl2
19) 2 CH3 CH2 CH2Li + CuI (CH3 CH2 CH2)2CuLi + LiI
20) 1. Li
2. CuI
21)
22)
23)
24)
7
Answer Key
Testname: CH03-SHORT ANSWER
25)
26)
27)
28)
29)
30)
31) alkene metathesis
32) (E)-4-octene, (Z)-4-octene, and ethene (or ethylene)
33) (E)-4,5-dimethyl-4-octene, (Z)-4,5-dimethyl-4-octene, and ethene (or ethylene)
34) cycloheptene and ethene (or ethylene)
8
Answer Key
Testname: CH03-SHORT ANSWER
35)
9
Module 4 – short answer
1) Propose a mechanism for the following reaction:
2) Predict the major product of the reaction below and provide a stepwise mechanism which accounts for its
formation.
CH3 (CH2 )6 CH2 OH + HBr
3) Provide the structure of the major organic product in the reaction below.
4) Name and provide the structure of the major organic product which results when (R)-3,3-dimethyl-2-butanol
is heated in the presence of HBr.
5) Provide the major organic product of the reaction below.
6) Provide the major organic product of the reaction below.
7) Provide the major organic product of the reaction below.
1
8) Provide the major organic product of the reaction below.
9) Provide the structure of the major organic product of the following reaction.
10) Provide the structure of the major organic product of the following reaction.
11) Provide the structure of the major organic product in the reaction below.
1. TsCl, pyridine
PhCH2 CH2 OH
2. NaCN, acetone
12) Provide the structure of the major organic product of the following reaction.
13) Provide the major organic product of the reaction below.
14) Provide the major organic product of the reaction below.
2
15) Provide the major organic product of the reaction below.
16) Which of the following alcohols, when heated with H2 SO4 , will undergo dehydration more rapidly? Explain.
17) Propose a detailed, step-by-step mechanism for the reaction pathway shown below.
18) Propose a detailed, step-by-step mechanism for the reaction pathway shown below.
19) Draw all likely products of the following reaction and circle the product you expect to predominate.
2-pentanol
H2 SO4
20) Draw all likely products of the following reaction and circle the product you expect to predominate.
21) Provide the structure of the major organic product in the reaction below.
3
22) Provide the structure of the major organic product of the following reaction.
23) Provide the major organic product of the reaction below.
24) Provide the major organic product of the reaction below.
25) Provide the major organic product of the reaction below.
26) Provide the major organic product of the reaction below.
27) Provide the major organic product of the reaction below.
4
28) Propose a mechanism for the following reaction:
29) Provide the structure of the major organic product of the following reaction.
30) Provide the structure of the major organic product of the following reaction.
31) Provide the major organic product of the following reaction.
32) Provide the major organic product in the reaction below.
33) Provide the major organic product in the reaction below.
5
34) Provide the structure of the major organic product of the following reaction.
35) Provide the major organic product of the reaction below.
36) Provide the major organic product of the following reaction.
37) Provide the major organic product of the following reaction.
38) Provide the major organic product of the following reaction.
39) Provide the major organic product of the following reaction.
6
40) Provide the intermediate and product of the reaction shown below.
41) What sequence of reagents can be used to accomplish the conversion shown below?
7
Answer Key
Testname: CH04-SHORT ANSWER
1)
2)
3)
4) 2-bromo-2,3-dimethylbutane
5)
6)
7)
8
Answer Key
Testname: CH04-SHORT ANSWER
8)
9)
10)
11) PhCH2 CH2 CN
12)
13)
14)
15)
16) b) will undergo dehydration more rapidly because it produces a secondary benzylic carbocation, which is more stable
than secondary carbocation.
9
Answer Key
Testname: CH04-SHORT ANSWER
17)
18)
19)
20)
21)
22)
23)
10
Answer Key
Testname: CH04-SHORT ANSWER
24)
25)
26)
27)
28)
29)
11
Answer Key
Testname: CH04-SHORT ANSWER
30)
31)
32)
33)
34)
35)
plus enantiomer
36)
37)
12
Answer Key
Testname: CH04-SHORT ANSWER
38)
39)
40)
41) 1. Mg, Et2 O
2. Oxirane (epoxide)
3. H3 O+
4. PCC
the reaction sequence is:
13
Question 1.
.
Type of reaction: Hydrogenation of alkynes (anti addition of hydrogen)
Mechanism
.
(NH2
нас,
A CHâ‚‚
CH3
CH3
сна
CH3
CH3
Na
CH3
CH3
H3C
H₃C
CH3
CH3
ΝΗ)
H
There are essentially two types of hydrogenation reactions of alkynes: the ones that lead to cis-alkenes and the ones to
lead to trans-alkenes. In the first, usually Platinum catalyst are used and hydrogens are bonded to the surface of the
metal, inducing a syn-addition of the hydrogens. In the latter, however, a free radical mechanism is induced by the
presence of an elemental metal such as lithium or sodium and therefore the most stable intermediates are formed
according to the VSEPR theory, leading to the trans addition of the hydrogens as shown above.

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