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Draw the resonance structure indicated by the arrows. - PowerPoint PPT Presentation


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Draw the resonance structure indicated by the arrows. 1). 2). 3). Label each atom with the correct hybridization. 4). sp 3. sp 3. sp 3. sp 3. sp 3. sp 3. 5). sp 3. sp 2. sp 2. sp 3. sp 2. 6). sp 2. sp. sp. sp 3. 7) Draw H 2 NCH 2 + in its second best resonance structure.

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slide2

3)

Label each atom with the correct hybridization.

4)

sp3

sp3

sp3

sp3

sp3

sp3

slide3

5)

sp3

sp2

sp2

sp3

sp2

6)

sp2

sp

sp

sp3

slide4

7) Draw H2NCH2+ in its second best resonance structure.

8) Draw the best Lewis structure for CH3CHO, a neutral molecule

slide5

9) Draw the Lewis structure for CH3COOH, a neutral molecule.

10) Draw the Lewis structure for N2H2, a neutral molecule.

slide6

11) Draw in the electron flow arrows in on the left hand structure that lead to the resonance structure on the right.

12) In the empty box, draw the best resonance structure of the left-hand compound, and draw one or more electron-flow arrows on the preexisting structure that lead to the new structure.

slide7

13)

14)

slide9

Label each of the following as an ionic or covalently bonded compound.

  • NaF
  • BrCl
  • NaOCHe

ionic

covalent

ionic

Calculate the formal charge of nitrogen in each of the following compounds.

a)

b)

FC = 5 – (4 + (1/2(4))) = -1

FC = 5 – (2 + (1/2(6))) = 0

FC = 5 – (0 + (1/2(8))) = +1

slide10

Draw the Lewis structure.

  • (CH3(OH2))+
  • CH3NO2

Draw all possible isomers of C2H4O.

slide11

Are each of the following pairs isomers or resonance structures?

a)

b)

Neither, different formulas

Isomers, same formula but different arrangement of atoms.

slide17

Convert into Lewis structures.

a) (CH3)3COH

b) CH3COCH2Br

slide19

Which is the weakest of the indicated bonds?

A is the weakest bond due to it being composed of a sp3 and sp2 hybridized orbital, thus having the least amount of S character

B is the weakest, b/c bond strength increases across a row in the periodic table and N is to the left of O.

slide21

Draw the products and determine if the reaction occurs.

pka=0.2

pka=16

Products favored

pka=-7

pka=5

reactants favored

slide22

Which is the strongest base?

HBr, HCl or HF

HF, b/c it is the weakest acid.

Identify the most acidic hydrogen.

C is the most acidic hydrogen b/c it’s bonded to an sp hybridized carbon.

slide23

Draw the products of each reaction and label the starting materials as a Lewis acid and base.

LB

LA

LB

LA

slide24

1) Complete the following acid-base reaction.

2) Complete the following acid-base reaction. Draw only the organic products.

slide25

3)

4) Choose the strongest acid.

Both Cl and Br are further right than S. And Br is further down than Cl. So most acidic.

slide26

5)

Both O and S are further right than P. And S is further down than O. So most acidic.

6) Choose the weakest acid.

C is further left than O and S so weakest acid.

slide27

7) The following compound has two stereoisomers. One has a dipole of 0 D, and the other has a dipole moment of 2.95 D. Draw the structure of the stereoisomer with dipole moment of 2.95 D.

slide28

8) Rank the three compounds from least acidic (rank 1) to most.

1

3

2

We know Si is more acidic than C because it is below C in the same column. Although Si and O can’t be compared directly, O is much more acidic.

slide29

9) Rank the following compounds from most acidic (rank 1) to least.

3

2

4

1

Acidity is based on the electron withdrawing effect of the four different substituents. O is the most electronegative, furthest up and to the right, and thus gives the most acidic compd. And Cl is more electronegative than Br b/c electronegativity increases up the column.

slide30

10) Draw the electron-flow arrows that lead from starting materials to products in this acid–base reaction.

11)

slide31

1) Draw an aldehyde.

RCHO

2) Draw an ester.

RCOOR or RCO2R

slide32

3) Draw a sulfide.

RSR

4) Draw 1,1-dimethylcyclohexane.

slide33

5) Draw 2,2,4-trimethylhexane.

6) Draw trans-1,3-dibromocyclobutane.

slide35

9) Draw 2,2,4,4-tetramethylhexane

10) Draw the structural formula of an alkane that has eight carbons and only primary hydrogens.

Primary hydrogens are attached to carbons attached to only one other carbon.

slide36

11) Draw the conformation favored by 1,2-dichloroethane at equilibrium in the liquid phase by following this procedure.

anit

gauche

The gauche conformer is favored in the liquid phase due to a polar effect. However, for this class I would accept the anit conformer as your answer, which would be correct if in the gas form.

slide37

12) Draw cis-3-ethyl-1-isopropylcyclohexane in its lowest energy conformation

13) Draw trans-1-bromo-3-methylcyclohexane in its lowest energy conformation

slide38

1) Draw the Lewis structure of HNO3.

2) What is the formal charge of the following compound?

FC = 4 – (2 + (1/2)(6)) = -1

slide40

4) What are the hybridizations of the numbered carbons?

sp3

sp2

5) Which of the following compounds has the largest net dipole? Draw the contributing dipoles of the compound you choose.

CO2 H2O CHCl3

slide41

6) Draw the product of the following reaction. (Label the Lewis Acid and Base)

LA

LB

7) Which molecule plays the role of acid?

HNO3 + H2SO4 → HSO4– + H2NO3+

acid

slide42

8) Using pKa values from the table, determine if the following reaction will occur.

4.75

15.5

pKa of the conjugate acid is larger than that of the acid so the reaction favors the products.

slide43

9) Which is the strongest base?

LiOH LiF LiCH3

LiCH3 is the strongest base because the acid it forms when the anion is protonated is very weak.

10) What intermolecular forces does the following molecule exhibit?

It possesses Van der Waals and dipole-dipole interactions.

slide44

11) Which of the following has the highest boiling and why?

CBr3CH3 CH3OCH3 CH3NH2

CH3NH2 has the highest boiling point because it possesses the same intermolecular forces as the first two molecules, but also has hydrogen bonding capabilities.

12) Label the electrophile and nucleophile. Then if the reaction occurs, draw the products.

Nu

E

slide45

13) Name the following compound.

2-sec-butyl-4-ethyl-1-methylcyclohexane

14) Which of the following has the highest melting point? Why?

a) 2-methylbutane

b) 2,2',3-dimethylbutane

c) 2,2',3,3'-tetramethylbutane

c) 2,2',3,3'-tetramethylbutane has the highest metlign point due to its high symmetry giving it the ability to pack close together in the crystal lattice.

slide46

15) Draw 2-chloro-4-ethyl-3-methylheptane

Draw the most stable form of trans-1-bromo-3-ethylcyclohexane.

More stable

slide47

Using Newman projections, draw all the staggered conformations of 1-chloropropane, label the anti and gauche forms.