Reaction Hydrogenation of Alkynes Questions

Ch07- homework

  1. Provide the major organic product in the reaction below.

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  1. Provide the structure of the major organic product(s) in the reaction below.

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  1. 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

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  1. Complete the following tree of reactions by giving the major products. (don’t worry about g)

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  1. Draw an acceptable structure for 3- sec– butyl- 1- heptyne.

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  1. 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

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  1. Describe a sequence of reactions by which cis– 2- pentene could be prepared from acetylene.

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  1. Provide an acceptable name for the compound shown.

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  1. Provide the structure of the major organic product(s) in the reaction below.

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  1. Describe a sequence of reactions by which trans– 2- pentene can be prepared from propyne.

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  1. Provide the systematic name of the compound shown.

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  1. Draw an acceptable structure for 2- hexyne.

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  1. Provide the sequence of reagents that are needed to accomplish the multistep synthesis below.

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  1. Provide the major organic product in the reaction below.

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  1. Provide the structure of the major organic product of the following reaction.

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  1. Describe a sequence of reactions by which the aldehyde CH3CH2CH2CH2CHO could be prepared from acetylene.

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  1. Write structures and give IUPAC names for all alkynes with molecular formula C5H8.

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  1. Which hydrogens are more acidic, those of benzene or those of cyclohexane? Why?

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  1. Provide the structure of the major organic produt that results when 2- butyne is treated with 1 equivalent of HCl.

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  1. Provide the major organic product in the reaction below.

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  1. Why are terminal alkynes more acidic than other hydrocarbons?

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  1. Provide the major organic product in the reaction below.

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  1. Explain why HCMN is a stronger acid than HCMCH.

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  1. Give the reagents for the following reaction.

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  1. Provide the structure of the major organic produt that results when 2- butyne is treated with HgSO4/H2SO4 in water

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  1. Describe a sequence of reactions by which butylbenzene can be prepared from phenylacetylene.

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  1. Provide the structure of (2E,4E)- 2- chloro- 2,4- octadiene.

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  1. Provide the systematic name of the compound shown.

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  1. word image 75 Provide the structure of the major organic product of the following reaction.

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  1. Provide the structure of the major organic product of the following reaction.

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  1. Provide the structure of the major organic product of the following reaction.

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  1. Name the following compound.

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  1. Provide the major organic product in the reaction below.

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  1. Provide the structure of the major organic product(s) in the reaction below.

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  1. Provide the structure of the major organic produt that results when 2- butyne is treated with H2 in the presence of Lindlar’s Catalyst.

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  1. Provide the major organic product in the reaction below.

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  1. Provide the major organic product of the following reaction sequence.

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  1. Provide the major organic product in the reaction below.

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  1. Provide the major organic product of the following reaction sequence.

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  1. Describe a sequence of reactions by which 3- heptyne can be straightforwardly prepared from acetylene.

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  1. Give the systematic name of the compound shown below.

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  1. Provide the major organic product in the reaction below.

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  1. Provide the structure of the major organic product of the following reaction.

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  1. Complete the following reaction.

Na, NH3

3

hexyne

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  1. Provide the sequence of reagents that are needed to accomplish the multistep synthesis below.

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1)

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2)

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3) CH3CH2CMCCH2Ph

4)

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5)

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6)

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  1. 1) NaNH2
    1. CH3CH2Br
    2. NaNH2
    3. CH3Br
    4. H2, Lindlar’s catalyst
  2. 7,7- dichloro- 5,5- dimethyl- 3- heptyne or 7,7- dichloro- 5,5- dimethylhept- 3- yne

9)

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  1. 1) NaNH2
    1. CH3CH2Br
    2. Na, NH3
  2. 5,6,6- trimethyl- 1- heptyne 12)

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13) 1. NaNH2

  1. CH3CH2I
  2. Na, NH3

14)

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15)

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16) 1)

NaNH2

2)

CH3CH2CH2Br

3)

disiamylborane

4) 17)

H2O2, – OH

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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)

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20)

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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)

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  1. Because nitrogen is more electronegative than carbon.
  2. 1. NaNH2, 2. CH3CH2Br, 3. NaNH2, 4. CH3CH2Br, 5. 2 Br2 25)

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26) 1) NaNH2

  1. CH3CH2Br
  2. H2, Pt

27)

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28) (E)- 5- methyl- 5- hepten- 1- yne

29)

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30)

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31)

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32) cis– 4,5- dimethyl- 4- hepten- 2- yne or (Z)- 4,5- dimethyl- 4- hepten- 2- yne

33)

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34)

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35)

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36)

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37)

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38)

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39)

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  1. 1) NaNH2
    1. CH3CH2Br
    2. NaNH2
    3. CH3CH2CH2Br
  2. 1,7- dimethyl- 1,3- cycloheptadiene

42)

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43)

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  1. trans– 3- hexene
  2. 1. NaNH2
    1. CH3CH2I
    2. H2, Lindlar catalyst

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