Ch07- homework
- Provide the major organic product in the reaction below.
- Provide the structure of the major organic product(s) in the reaction below.
- Provide the structure of the major organic product(s) in the reaction below.
2
CH
3
CH
2
C
M
CH
1. NaNH
2
. PhCH
2
Br
- Complete the following tree of reactions by giving the major products. (don’t worry about g)
- Draw an acceptable structure for 3- sec– butyl- 1- heptyne.
- Provide the structure of the major organic product(s) in the reaction below.
Na, NH3
CH
3
CH
2
N
C
M
C
N
CH
3
- Describe a sequence of reactions by which cis– 2- pentene could be prepared from acetylene.
- Provide an acceptable name for the compound shown.
- Provide the structure of the major organic product(s) in the reaction below.
- Describe a sequence of reactions by which trans– 2- pentene can be prepared from propyne.
- Provide the systematic name of the compound shown.
- Draw an acceptable structure for 2- hexyne.
- Provide the sequence of reagents that are needed to accomplish the multistep synthesis below.
- Provide the major organic product in the reaction below.
- Provide the structure of the major organic product of the following reaction.
- Describe a sequence of reactions by which the aldehyde CH3CH2CH2CH2CHO could be prepared from acetylene.
- Write structures and give IUPAC names for all alkynes with molecular formula C5H8.
- Which hydrogens are more acidic, those of benzene or those of cyclohexane? Why?
- Provide the structure of the major organic produt that results when 2- butyne is treated with 1 equivalent of HCl.
- Provide the major organic product in the reaction below.
- Why are terminal alkynes more acidic than other hydrocarbons?
- Provide the major organic product in the reaction below.
- Explain why HCMN is a stronger acid than HCMCH.
- Give the reagents for the following reaction.
- Provide the structure of the major organic produt that results when 2- butyne is treated with HgSO4/H2SO4 in water
- Describe a sequence of reactions by which butylbenzene can be prepared from phenylacetylene.
- Provide the structure of (2E,4E)- 2- chloro- 2,4- octadiene.
- Provide the systematic name of the compound shown.
Provide the structure of the major organic product of the following reaction.
- Provide the structure of the major organic product of the following reaction.
- Provide the structure of the major organic product of the following reaction.
- Name the following compound.
- Provide the major organic product in the reaction below.
- Provide the structure of the major organic product(s) in the reaction below.
- Provide the structure of the major organic produt that results when 2- butyne is treated with H2 in the presence of Lindlar’s Catalyst.
- Provide the major organic product in the reaction below.
- Provide the major organic product of the following reaction sequence.
- Provide the major organic product in the reaction below.
- Provide the major organic product of the following reaction sequence.
- Describe a sequence of reactions by which 3- heptyne can be straightforwardly prepared from acetylene.
- Give the systematic name of the compound shown below.
- Provide the major organic product in the reaction below.
- Provide the structure of the major organic product of the following reaction.
- Complete the following reaction.
Na, NH3
3
–
hexyne
- Provide the sequence of reagents that are needed to accomplish the multistep synthesis below.
1)
2)
3) CH3CH2CMCCH2Ph
4)
5)
6)
- 1) NaNH2
- CH3CH2Br
- NaNH2
- CH3Br
- H2, Lindlar’s catalyst
- 7,7- dichloro- 5,5- dimethyl- 3- heptyne or 7,7- dichloro- 5,5- dimethylhept- 3- yne
9)
- 1) NaNH2
- CH3CH2Br
- Na, NH3
- 5,6,6- trimethyl- 1- heptyne 12)
13) 1. NaNH2
- CH3CH2I
- Na, NH3
14)
15)
16) 1) | NaNH2 |
2) | CH3CH2CH2Br |
3) | disiamylborane |
4) 17) | H2O2, – OH |
18) Benzene. The carbon hybridization of benzene is sp2 while that of cyclohexane is sp3. The more s character in benzene causes its hydrogens to be more acidic than those of cyclohexane.
19)
20)
21) The carbanion which results upon deprotonation of a terminal alkyne has the lone pair of electrons in an sp hybrid orbital. The greater % s character of this orbital gives the orbital a significantly lower energy.
22)
- Because nitrogen is more electronegative than carbon.
- 1. NaNH2, 2. CH3CH2Br, 3. NaNH2, 4. CH3CH2Br, 5. 2 Br2 25)
26) 1) NaNH2
- CH3CH2Br
- H2, Pt
27)
28) (E)- 5- methyl- 5- hepten- 1- yne
29)
30)
31)
32) cis– 4,5- dimethyl- 4- hepten- 2- yne or (Z)- 4,5- dimethyl- 4- hepten- 2- yne
33)
34)
35)
36)
37)
38)
39)
- 1) NaNH2
- CH3CH2Br
- NaNH2
- CH3CH2CH2Br
- 1,7- dimethyl- 1,3- cycloheptadiene
42)
43)
- trans– 3- hexene
- 1. NaNH2
- CH3CH2I
- H2, Lindlar catalyst