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Chemistry > Chapter 14- Introduction to Organic Chemistry > Flashcards

Chapter 14- Introduction to Organic Chemistry Flashcards

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1
Q

chap 14:

bonds in a C=C bond

A

one pi and one sigma

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2
Q

types of structural isomerism

A
  1. positional isomerism
  2. functional group isomerism
  3. chain isomerism
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3
Q

describe positional isomerism

A

the position of the functional group varies in each isomer

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4
Q

describe functional group isomerism

A

the functional group varies in each isomer

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5
Q

describe chain isomerism

A

the chain differs in both isomers; for example one could be a straight chain and the other could be branched

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6
Q

types of stereoisomerism

A
  1. cis/Z and trans/E

2. optical

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7
Q

describe cis/ trans isomerism

A
  1. only happens with alkenes
  2. in cis/Z, the same type of atoms are on the same side of the compound and in trans/E, the atoms are on different sides
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8
Q

describe optical isomerism

A

contains a chiral centre

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9
Q

chap 15:

what is true for every nucleophile?

A

contains a lone pair (donates a pair of electrons)

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10
Q

crude oil contains what type of organic compounds ?

A

alkanes

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11
Q

before fractional distillation, what happens to crude oil?

A

vaporization

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12
Q

initiation, propagation and termination reactions

A

initiation:
Cl2 = 2Cl⚫️ (condition: UV light)

propagation:
CH4 + Cl⚫️ = ⚫️CH3 + HCl

termination:
⚫️CH3 + Cl⚫️ = CH3Cl

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13
Q

Give the condition and reagent of the reaction when hydrogen is added to alkenes. What is the product formed?

A

reagent: H2
condition: Ni catalyst, 140 deg cel

product: alkane

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14
Q

Give the condition and reagent of the reaction when steam is added to alkenes. What is the product formed?

A

reagent: H2O
condition: H3PO4 catalyst, 330 deg cel, 6MPa pressure

product: alcohol

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15
Q

Give the condition and reagent of the reaction when hydrogen halides are added to alkenes. What is the product formed?

A

reagent: HX (X=F, Cl, Br, I)
condition: alkene is bubbled through concentrated solution of HX at room temperature

product: halogenoalkane

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16
Q

State the Markonikov’s rule

A

the major product is the one where the hydrogen attaches itself to the carbon with the most number of hydrogens (or where the halogen atom attaches to the carbon with least number of hydrogens)

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17
Q

What mechanism is for alkenes?

A

electrophilic addition

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18
Q

what happens when cold dilute acidified manganate is added to alkenes?

A
  1. a diol is formed
  2. solution turns from pale purple to colorless
  3. reaction is done at room temperature
19
Q

what happens when hot concentrated manganate is added to alkenes?

A

no R groups attached to C: CO2
1 R group attached to C: aldehyde further oxidized to carboxylic acid
2 R groups attached to C: a ketone

20
Q

chap 16:

mechanism of halogenoalkanes

A

nucleophilic substitution

21
Q

Give the condition and reagent of the reaction when aqueous alkali is added to halogenoalkanes. What is the product formed?

A

reagent: NaOH
condition:

product: alcohol
(this is a nucleophilic substitution reaction)

22
Q

Give the condition and reagent of the reaction when alcoholic alkali is added to halogenoalkanes. What is the product formed?

A

reagent: NaOH (ethanol)
condition:

product: alkenes + water + NaX (X: halogen)
(this is an example of an elimination reaction)

23
Q

give the C-X bonds in ascending order

A

C-I (weakest) > C-Br, C-Cl, C-F (strongest)

24
Q

Give the condition and reagent of the reaction when CN (in ethanol) is added to halogenoalkanes. What is the product formed?

A

reagent: KCN (in ethanol)
condition: heat under reflux

product: nitrile (with an addition of one carbon atom)

25
Q

Give the condition and reagent of the reaction when NH3 in ethanol) is added to halogenoalkanes. What is the product formed?

A

reagent: NH3 (in excess)
condition: NH3 should be dissolved in ethanol, carried out under pressure

product: amine

26
Q

why is ammonia added in excess when halogenoalkanes are substituted with NH3?

A

so that we don’t get a mixture of amine products. because the amine will start to act as a nucleophile itself and will attack the halogenoalkane molecules forming secondary amines.

27
Q

describe SN2 mechanism

A
  1. primary halogenoalkane
  2. forms intermediate with 5 bonds
  3. 1 step reaction
28
Q

describe SN1 mechanism

A
  1. tertiary halogenoalkane

2. 2 step reaction

29
Q

chap 17:

Give the conditions and reagent of the reaction when a halogen halide is added to alcohol. What is the product formed?

A

reagent: HX
condition:

product: H2O + halogenoalkane

30
Q

Give the reagent of the reaction when a sodium metal is added to alcohol. What is the product formed?

A

reagent: Na

product: sodium alkoxide + hydrogen
the longer the chain, the less vigorous the reaction

31
Q

Give the conditions and reagent of the reaction when a carboxylic acid is added to alcohol. What is the product formed?

A

reagent: carboxylic acid
conditions: heat under reflux, strong acid catalyst (concentrated H2SO4)

product: ester + H2O

32
Q

Give the conditions of the reaction when an alcohol is dehydrated. What is the product formed?

A

conditions: Al2O3 as catalyst
product: alkene + H2O

33
Q

Give the conditions and reagent of the oxidation of alcohol. What is the product formed?

A

reagent: K2Cr2O7 (gives orange solution which turned green when alcohol is oxidized)
conditions: reaction needs to be heated and dilute sulfuric acid needs to be added

product:
1. with tertiary alcohol: no oxidation takes place
2. with secondary alcohol: ketone is formed
3. with primary alcohol: aldehyde is formed which further oxidizes to carboxylic acid

34
Q

what are the ways to make carboxylic acid?

A
  1. oxidation of primary alcohols
  2. hot concentrated manganate is added to alkenes
  3. hydrolysis of nitrile group
    (nitrile is refluxed with HCl (turn CN bond to COOH))
35
Q

how do you convert carboxylic acids to their corresponding primary alcohols? what are the reagents and conditions?

A
  1. by reduction
    reagent: LiAlH4
    condition: in dry ether at room temperature
36
Q

chap 18:

give the reagent and condition for oxidation of primary alcohol. what is the product formed?

A

reagent: K2Cr2O7
condition: acidified with H2SO4, heat the reaction mixture

product: aldehyde + water

37
Q

give the reagent and condition for oxidation of secondary alcohol. what is the product formed?

A

reagent: K2Cr2O7
condition: acidified with H2SO4, reaction must be heated

product: ketone + water

38
Q

give the reagents and conditions for the reduction of carbonyl compounds. what are the products formed?

A

reagent: NaBH4 / LiAlH4
condition for NaBH4: warming the solution
condition for LiAlH4: to be carried out in dry ether

reducing ketone give secondary alcohol
reducing aldehyde gives primary alcohol

39
Q

what mechanism takes places with carbonyl compounds and what are the reagents needed?

A

nucleophilic addition by using HCN as reagent

40
Q

the nitrile group can be reduced to what compound? what are the reagents needed?

A

an amine

reagent: Na (ethanol)

41
Q

2,4-DNPH gives positive for ketone and aldehyde. what is observed?

A

orange ppt

42
Q

name two reagents which give positive for only aldehydes

A

tollens’ and fehling’s

  1. tollens’ gives silver mirror
  2. fehling’s gives red/orange ppt
43
Q

what group gives positive for reaction with tri-iodomethane and what is observed?

A

CH3CO, yellow ppt is observed

44
Q

what is the only aldehyde that gives negative for tri-iodomethane?

A

ethanal

Chemistry (3 decks)

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