Cycloalkane

alkane
General fact intro

Introduction
Hydrogenation

Match
crossword

Gridnard reagent

Empowering
Reduction by zinc

SYNTHESIS OF ALKANE AND CYCLOALKA NE

Enhancing

Fill in the blank

Code translator Reduction by LiAlH4 and NaBH4

conclusion

True of false

END

I heard about cycloalkanebut I dont know what is that..

I wonder what is alkane actuallyanyone can explain it to me?

Can you give us the answers?

How can we synthesis both of them?

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Number of C atoms 1 2 3 4 5 6

Molecular formula CH4 C2H6 C3H8 C4H10 C5H12 C6H14

Name (n-alkane) Methane Ethane Propane Butane Pentane Hexane

Alkanes are hydrocarbons in which all the carbon-carbon bonds are single bond

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Number of C atoms 3

Molecular formula C3H6

Name (n-alkane) Cyclopropane

Shape

4
5 6

C4H8
C5H10 C6H12

Cyclobutane
Cyclopentane Cyclohexane

Cycloalkanes are the alkanes in which all or some of carbon atoms are arranged in a ring

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composed of tetrahedral, sp3 hybridized C atoms

named with the suffix -ane

two types of alkanes: acyclic alkanes (CnH2n+2), cycloalkanes(CnH2n)

no functional group and undergo few reactions

have only nonpolar C-C and C-H bonds

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1 mole H2 for alkenes

react with H2 in the present of metal catalysts (Pd, Ni and Pt) and in solvent EtOH hydrogenation of alkenes and alkynes

2 moles H2 for alkynes

C C C + H2

C + H2
Pd,Pt,Ni EtOH

Pd,Pt,Ni EtOH

C
Pd,Pt,Ni EtOH

C + H2

CH3
CH3C CH

CH3
C CH3
Acyclic Alkane

CH3 H
CH3 + Pd/Ni/Pt 2
EtOH

CH3
C CH3

CH3C H

H CH3

H2

Pd/Ni/Pt EtOH

Cyclic Alkane

H C H C C H + H2

C H + H2
Pd/Pt/Ni EtOH

Pd/Pt/Ni EtOH

H H H C C H

H H

1)

CH3

+ H2

Pd/Pt/Ni
EtOH

2)

CH3 CH2 CH CH CH3 + H2

Pd/Pt/Ni EtOH

3)

CH3

CH

CH

CH3

CH3CH2CH2CH3

1)

CH3

CH3

+ H2
2)

Pd/Pt/Ni
EtOH

CH3 CH2
3)

CH

CH

CH3 + H2

Pd/Pt/Ni EtOH

CH3 CH3 CH CH CH3

CH3

CH

CH

CH3 + H2

Pd/Pt/Ni EtOH

CH3CH2CH2CH3
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Grignard reagents are organomettalic compounds in which the metal is mostly magnesium.the general molecular formula is RMgX

Whose discover that?

R is an alkyl or aryl (based on a benzene ring) group

X is a halogen atom, usually chlorine, bromine, or iodine.

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

Mg

2+

OH

Br

Yes, I got alkane.

CH3CH2MgBr + H20 MgBr + H2O

CH3CH3

Mg(OH)Br

Mg(OH)Br

CH3CH2CH2MgBr + H20 CH3

CH3CH2CH2 CH3

Mg(OH)Br

CH3 + H2O MgBr

CH3 + Mg(OH)Br

What is the structure of R?

RMgBr

O R

R = ????

Answer :

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Zinc, Zn

Aqueous acid Reduction

R-X

Zn/CH3COOH

R-H

Acyclic Alkane

Br
CH3 CH2 CH H CH3

Zn/CH3COOH

CH3

CH2

C
H

CH3

Cyclic Alkane Br

Zn/CH3COOH

1)

CH3CH2CH2CH2Cl

Zn/CH3COOH

2)

CH2Br
Zn/CH3COOH

3)

CH3CH2CH2CH

CH2CH3

CH3CH2CH2CH

CH2CH3

CH2CH2F

CH2CH3

1)

CH3CH2CH2CH2Cl

Zn/CH3COOH

CH3CH2CH2CH3

2)

CH2Br
Zn/CH3COOH

CH3

3)

CH3CH2CH2CH

CH2CH3 Zn/CH3COOH CH3CH2CH2CH

CH2CH3

CH2CH2F

CH2CH3
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Reduction by lithium halide (LiAlH4) and sodium tetrahydridoborate (NaBH4)

Electrophiles accept electrons to form the bond LiAlH4 and NaBH4 function as nucleophiles

Primary and secondary alkyl halides are reduced with NaBH4 while 1o, 2o and 3o alkyl halides are reduced with LiAlH4

Alkane produce

Na H

B H H Cl

CH 2

CH 2

CH 3

CH 2

CH 2

CH 3 + NaCl

+ BH 3

polarized bond

EXAMPLE
CH3CH2CH2CH2Cl CH3
LiAlH4

CH3CH2CH2CH3 CH3

NaBH4

Br

CH3CH2CH2CH2Cl

LiAlH4

CH2CH2I

NaBH4

ErmmmI will try. Can you answer it?

CH2CH2Br

LiAlH4

CH3CH2CHCH2CH2CH3 CH2CH2Br

NaBH4

Well, Im done it.

DID YOU GET THE ANSWER?

CH3CH2CH2CH2Cl

LiAlH4

CH3CH2CH2CH3

CH2CH2I

NaBH4

CH2CH3

CH2CH2Br

LiAlH4

CH2CH3

CH3CH2CHCH2CH2CH3 CH2CH2Br

NaBH4

CH3CH2CHCH2CH2CH3 CH2CH3
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Corey-Posner, Whiteside-House Synthesis

Lithium dialkyl cuprate (R2CuLi)

Alkyl halide (R-X)

New alkane (R-R)

Organocopper compound (R-Cu)

Lithium halide (Li-X)

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

EXAMPLE
(CH3CH3)2CuLi + CH3CH2CH2CH2CH2Cl
Et2O

CH3CH2CH2CH2CH2CH2CH3 + CH3CH3Cu + LiCl CH2CH2Br + (CH3) 2CuLi

Et2O

CH2CH2 CH3

+ CH3Cu + LiBr

EXERCISE
Et2O

CH3CH2CH2CH2CH2I

+ (CH3)2CuLi

CI

)2CuLi

Et2O

(CH3CH2)2CuLi
CH3

Et2O

TRY UR BEST

ANSWER
CH3CH2CH2CH2CH2I + (CH3)2CuLi
Et2O

CH3CH2CH2CH2CH2 CH3
+ CH3Cu + LiI

CI

)2CuLi

Et2O

Cu + LiCl

(CH3CH2)2CuLi CH3

Et2O

CH3CH2 CH3

+ CH3CH2Cu CH3

+ LiBr

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Match the following item

Alkanes Cycloalkanes sp3 hybridized C atoms Hydrogenation Reduction

Metal catalyst + EtOH Alkanes CnH2n Zinc + aqueous acid CnH2n+2

Lets check the answers

Alkanes Metal catalyst + EtOH Cycloalkanes Alkanes sp3 hybridized C atoms CnH2n Hydrogenation Reduction Zinc + aqueous acid CnH2n+2

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M
Q A E R F H J L T T H

S
E G U I J B J M H K E

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M Q A E R F H J L T T H E A E

S E G U I J B J M H K E R A R

A W T E 5 G H V K R U R T L T

F A T A A I L J N E 1 C F K F

E T Y A L I O U R E 0 F Y Y U

S N G S W C T K O R 7 V U L I

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H S I P O K L T I T Y K 9 D Q

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O A E N A K L A G P I E T O L

P K L H T G F C B N U N N K J

A Q U E O U S A C I D 2 H P K

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1)
2)

3) 4) 5) 6)

The important components in hydrogenation of alkene and alkynes are and (EtOH). 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. Grignard reagent hydrolysis needs to be carried out. Reduction by zinc must be in the presented of The product of alkyl halide after undergoes reduction by lithium aluminium hydride is 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

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Whats he saying?
Use the secret code translator below to find out!

I VWFXGRLM - - - - - - - - RH LMV LU - - - - - - ZOPZMVH - - - - - - -

LU -GSV - - -

ZOPBO - - - - -

SZORWVH - - - - - - LU --

HBMGVHRH - - - - - - - -

ANSWER : REDUCTION OF ALKYL HALIDES IS ONE OF THE SYNTESIS OF ALKANES

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1. 1o, 2o and 3o alkyl halides are reduced with NaBH4

TRUE

FALSE

2. LiAlH4 and NaBH4 function as nucleophiles

3. We also can produce alkane through reduction of zinc 4. Primary and secondary alkyl halides are reduced with LiAlH4 5. C9H19CH2BR + LiAlH C9H19CH3

TRUE
TRUE

FALSE
FALSE

TRUE

FALSE You can do it!

TRUE

FALSE

Dont give up

Answer: 1) False 2) true 3) true 4) false 5) true

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CONCLUSION

SYNTHESIS
ALKANES + CYCLOALKANES

Hydrogenation of alkenes ( ) and alkynes ( ) Reduction of Alkyl Halides

Corey-Posner, Whiteside-House Synthesis

Grignard reagent hydrolysis R-Mg-X + H-OH Mg(OH)X R-H + Reduction by lithium aluminium hydride R-X
LiAlH4

Reduction by zinc in the presence of aqueous acid R-H

Zn/CH3COOH

R-H

R-H

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