organic mind map ppt
TRANSCRIPT
SYNTHESIS OF
ALKANE AND
CYCLOALKANE
Introduction
Enhancingconclusion
Empowering
alkane
Cycloalkane
General fact
Fill in the blank
True of false
crossword
MatchHydrogenation
Gridnard reagent
Reduction by zinc
END
Reduction by LiAlH
4
and NaBH4
Code translator
intro
I wonder what is alkane actually…
anyone can explain it to me?
I wonder what is alkane actually…
anyone can explain it to me?I heard about
cycloalkane…but I don’t know what is
that..
I heard about cycloalkane…but I don’t know what is
that..
How can we synthesis both of them?
How can we synthesis both of them?
Can you give us the answers?
Can you give us the answers?
BACK
Cn
H2n
+2
Alkane
Number of C atoms Molecular formula Name (n-alkane)1 CH4 Methane
2 C2H6 Ethane
3 C3H8 Propane
4 C4H10 Butane
5 C5H12 Pentane
6 C6H14 Hexane
Alkanes are hydrocarbons in which all the carbon-carbon bonds are
single bond
BACK
Cn
H2n
Cycloalkane
Number of C atoms Molecular formula Name (n-alkane) Shape
3 C3H6 Cyclopropane
4 C4H8 Cyclobutane
5 C5H10 Cyclopentane
6 C6H12 Cyclohexane
Cycloalkanes are the alkanes in which all or some of
carbon atoms are arranged in a ring
BACK
composed of tetrahedral,
sp3 hybridized C atoms
two types of alkanes: acyclic
alkanes (CnH2n+2),
cycloalkanes(Cn
H2n)
have only nonpolar C-C
and C-H bonds
no functional group and
undergo few reactions
named with the suffix -ane
BACK
HYDROGENATION OF ALKENES AND ALKYNES
hydrogenation of
alkenes and
alkynes
react with H2 in the present of metal
catalysts (Pd, Ni and Pt) and in solvent
EtOH
1 mole H2 for alkenes2 moles H2
for alkynes
C C + H2 C C
C C + H2 C C + H2 C C
C C + H2 C C
C C + H2 C C + H2 C C
Pd,Pt,NiPd,Pt,Ni
EtOHEtOH
EtOHEtOH EtOHEtOH
Pd,Pt,NiPd,Pt,Ni Pd,Pt,NiPd,Pt,Ni
CH3 CH3 CH3 H CH3
CH3C CH C CH3 + 2 CH3C C C CH3
CH3 H H CH3
Pd/Ni/Pt
EtOH
Acyclic Alkane
+ H2Pd/Ni/Pt
EtOH
Cyclic Alkane
HYDROGENATION OF ALKYNES
H C C H + H2
C C + H2 C CH
H
H
HH
H
H
H
H
H
Pd/Pt/Ni
EtOH
Pd/Pt/Ni
EtOH
1)
2)
3)
CH3
+ H2Pd/Pt/Ni
EtOH
CH2 CH CH CH3
CH3
+ H2
Pd/Pt/Ni
EtOH
CH3 CH CH CH3CH3CH2CH2CH3
1)
2)
3)
CH3
+ H2Pd/Pt/Ni
EtOH
CH3
CH2 CH CH CH3
CH3
+ H2
Pd/Pt/Ni
EtOH CH3 CH CH CH3
CH3
CH3 CH CH CH3CH3CH2CH2CH3+ H2
Pd/Pt/Ni
EtOH
BACK
X is a halogen atom, usually chlorine,
bromine, or iodine.
R is an alkyl or aryl
(based on a benzene
ring) group
Grignard reagents are
organomettalic compounds in which the
metal is mostly
magnesium.the general molecular formula is
RMgX
Whose discover that?
Whose discover that?
It is discoverer by French chemist Victor Grignard, who was a
co recipient of the 1912 Nobel Prize for Chemistry for this
work
It is discoverer by French chemist Victor Grignard, who was a
co recipient of the 1912 Nobel Prize for Chemistry for this
work
Grignard reagents will
react with compounds containing
acidic hydrogen
atoms
Hydrogen atoms
attached to electronegative atoms (e.g. S, N,
O)
Reaction of Grignard reagent
with water to produce
alkane
H3C-Mg-Br H-O H
H3C-H Mg2+
OH Br+ + + +-
Yes, I got alkane.Yes, I got alkane.
CH3CH2MgBr + H20 CH3CH3 + Mg(OH)Br
MgBr
+ H2O + Mg(OH)Br
CH3CH2CH2MgBr + H20 CH3CH2CH2 + Mg(OH)Br CH3 CH3
CH3
MgBr
+ H2O
CH3
+ Mg(OH)Br
What is the structure of R?
H O
R
+RMgBr
R = ????
Answer :
BACK
Reduction
Aqueous acid
Zinc, Zn
R-X R-HZn/CH3COOH
Br
CH3 CH2 CH CH3
H
CH3 CH2 C CH3
H
Br
H
Zn/CH3COOH
Acyclic Alkane
Zn/CH3COOH
Cyclic Alkane
1)
2)
3)
CH3CH2CH2CH2Cl
Zn/CH3COOH
CH2Br
Zn/CH3COOH
CH3CH2CH2CH CH2CH3
CH2CH2F
CH3CH2CH2CH CH2CH3
CH2CH3
1)
2)
3)
CH3CH2CH2CH2Cl
Zn/CH3COOH CH3CH2CH2CH3
CH2Br
Zn/CH3COOH
CH3
CH3CH2CH2CH CH2CH3
CH2CH2F
CH3CH2CH2CH CH2CH3
CH2CH3
Zn/CH3COOH
BACK
Reduction by lithium halide (LiAlH4) and sodium tetrahydridoborate
(NaBH4)
Reduction by lithium halide (LiAlH4) and sodium tetrahydridoborate
(NaBH4)
LiAlH4 and NaBH4 function as
nucleophiles
LiAlH4 and NaBH4 function as
nucleophiles
Electrophiles accept
electrons to form the
bond
Electrophiles accept
electrons to form the
bondPrimary and
secondary alkyl halides are
reduced with NaBH4 while 1o, 2o
and 3o alkyl halides are
reduced with LiAlH4
Primary and secondary alkyl
halides are reduced with
NaBH4 while 1o, 2o and 3o alkyl halides are
reduced with LiAlH4
H B
H
H
HNa Cl CH2 CH2 CH3
polarized bond
+-CH2 CH2 CH3H NaCl
BH3
+
+
Alkane produce
EXAMPLE
LiAlH4LiAlH4
CH3CH2CH2CH2Cl
CH3
CH3CH2CH2CH3
CH3
Br
NaBH4NaBH4
CH3CH2CH2CH2Cl
CH2CH2I
CH2CH2Br
CH3CH2CHCH2CH2CH3
CH2CH2Br
LiAlH4
LiAlH4
NaBH4
NaBH4
Can you answer
it?
Ermmm…I will try.
CH3CH2CH2CH2Cl
CH2CH2I
CH2CH2Br
CH3CH2CHCH2CH2CH3
CH2CH2Br
LiAlH4
LiAlH4
NaBH4
NaBH4
DID YOU GET THE ANSWER?
CH3CH2CH2CH3
CH2CH3
CH2CH3
CH3CH2CHCH2CH2CH3
CH2CH3
Well, I’m done it.Well, I’m done it.
BACK
Corey-Posner, Whiteside-House Synthesis
Lithium dialkyl cuprate (R2CuLi)Lithium dialkyl
cuprate (R2CuLi)Alkyl halide
(R’-X)Alkyl halide
(R’-X)
New alkane
(R-R’)
New alkane
(R-R’)
Organocopper compound
(R-Cu)
Organocopper compound
(R-Cu)
An organic compound that involves the
reaction of a lithium dialkyl cuprate with an alkyl halide to form a
new alkane, an organocopper
compound and a lithium halide
Lithium halide
(Li-X)
Lithium halide
(Li-X)
R2CuLi + R’-X R-R’ + R-Cu + Li-X
EXAMPLE
(CH3CH3)2CuLi + CH3CH2CH2CH2CH2Cl
CH3CH2CH2CH2CH2CH2CH3 + CH3CH3Cu + LiCl
Et2O
CH2CH2Br + (CH3) 2CuLi
CH2CH2 CH3 + CH3Cu + LiBr
Et2O
EXERCISE
CH3CH2CH2CH2CH2I + (CH3)2CuLi
CI + ( )2CuLi
+ (CH3CH2)2CuLi
CH3
Et2O
Et2O
Et2O
TRY UR BEST
TRY UR BEST
CH3CH2CH2CH2CH2I + (CH3)2CuLi
CI + ( )2CuLi
+ (CH3CH2)2CuLi
CH3
Et2O
Et2O
Et2O
ANSWER
CH3CH2CH2CH2CH2 CH3
+ CH3Cu + LiI
+ Cu + LiCl
+ CH3CH2Cu + LiBr
CH3
CH3CH2
CH3
BACK
Match the following item
Alkanes
Cycloalkanes
sp3 hybridized C atoms
Hydrogenation
Reduction
Metal catalyst + EtOH
Alkanes
CnH2n
Zinc + aqueous acid
CnH2n+2
Let’s check the answers
Alkanes
Cycloalkanes
sp3 hybridized C atoms
Hydrogenation
Reduction
Metal catalyst + EtOH
Alkanes
CnH2n
Zinc + aqueous acid
CnH2n+2
BACK
M S A F E S D F 4 K H Y O P A
Q E W A T N E V L O S S A K Q
A G T T Y G R O P K I A E L U
E U E A A S E D Y W P I N H E
R I 5 A L W R T G A O D A T O
F J G I I C Q E S T K L K G U
H B H L O T A O P E L H L F S
J J V J U K E T W R T U A C A
L M K N R O R A A E I Y G B C
T H R E E R T S H L T O P N I
T K U 1 0 7 3 R D C Y R I U D
H E R C F V B M N L K S E N 2
E R T F Y U G V D 2 9 P T N H
A A L K Y L H A L I D E O K P
E R T F U I H T E W Q A L J K
Tips: the arrows can be…
M S A F E S D F 4 K H Y O P A
Q E W A T N E V L O S S A K Q
A G T T Y G R O P K I A E L U
E U E A A S E D Y W P I N H E
R I 5 A L W R T G A O D A T O
F J G I I C Q E S T K L K G U
H B H L O T A O P E L H L F S
J J V J U K E T W R T U A C A
L M K N R O R A A E I Y G B C
T H R E E R T S H L T O P N I
T K U 1 0 7 3 R D C Y R I U D
H E R C F V B M N L K S E N 2
E R T F Y U G V D 2 9 P T N H
A A L K Y L H A L I D E O K P
E R T F U I H T E W Q A L J K
BACK
1) The important components in hydrogenation of alkene and alkynes are …… and …… (EtOH).
2) Reduction of alkyl halide can be carried out through …… processes which are Grignard reagent hydrolysis, reduction by zinc in the presence of aqueous acid and reduction by lithium aluminium hydride.
3) Grignard reagent hydrolysis needs …… to be carried out.4) Reduction by zinc must be in the presented of ……5) The product of alkyl halide after undergoes reduction by
lithium aluminium hydride is……6) Corey-Posner, Whiteside-House synthesis is an organic
reaction of a lithium dialkyl cuprate with a/an …… to form a new alkane, an organocopper compound and a lithium halide.
1) The important components in hydrogenation of alkene and alkynes are metal catalyst and solvent (EtOH).
2) Reduction of alkyl halide can be carried out through three processes which are Grignard reagent hydrolysis, reduction by zinc in the presence of aqueous acid and reduction by lithium aluminium hydride.
3) Grignard reagent hydrolysis needs water to be carried out.4) Reduction by zinc must be in the presented of aqueous
acid.5) The product of alkyl halide after undergoes reduction by
lithium aluminium hydride is alkane.6) Corey-Posner, Whiteside-House synthesis is an organic
reaction of a lithium dialkyl cuprate with an alkyl halide to form a new alkane, an organocopper compound and a lithium halide.
BE THE BEST AMONG THE BEST
BE THE BEST AMONG THE BEST
BACK
What’s he saying?Use the secret code translator below to find out!
ANSWER : REDUCTION OF ALKYL HALIDES IS ONE OF THE SYNTESIS OF ALKANES
I V W F X G R L M LU Z O P B O S Z O R W V H - - - - - - - - - - - - - - - - - - - - - - -
R H L M V L U G S V H B M G V H R H L U - - - - - - - - - - - - - - - - - - - -
Z O P Z M V H- - - - - - -
BACK
1. 1o, 2o and 3o alkyl halides are reduced with NaBH4TRUE FALSE
2. LiAlH4 and NaBH4 function as nucleophiles TRUE FALSE
3. We also can produce alkane through reduction of zinc
TRUE FALSE
4. Primary and secondary alkyl halides are reduced with LiAlH4
TRUE FALSE
5. C9H19CH2BR + LiAlH C9H19CH3TRUE FALSE
You can do it!
You can do it!
Don’t give upDon’t give up
Answer: 1) False 2) true 3) true 4) false 5) true
BACK
SYNTHESIS
ALKANES
+ CYCLOALK
ANES
SYNTHESIS
ALKANES
+ CYCLOALK
ANESHydrogenation of alkenes ( ) and alkynes
( )
Hydrogenation of alkenes ( ) and alkynes
( )
Corey-Posner, Whiteside-House
Synthesis
Corey-Posner, Whiteside-House
Synthesis
Reduction of Alkyl HalidesReduction of Alkyl Halides
Grignard reagent hydrolysis
R-Mg-X + H-OH R-H + Mg(OH)X
Reduction by lithium aluminium hydride
R-X R-H
Reduction by zinc in the presence of aqueous
acid
R-H R-H
LiAlH4
Zn/CH3COOH
CONCLUSION
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