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CHM 1321 Assignment 1 Answers: CN H H H H H

This document contains an organic chemistry assignment with questions requiring drawing Lewis structures, constructing a portion of the periodic table, drawing structures of organic compounds with given formulas, naming structures, indicating dipole moments of bonds, illustrating hybridization and drawing molecular orbital structures. The assignment covers topics including Lewis structures, the periodic table, structural isomers, functional groups, polarity, hybridization and molecular orbitals.

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CHM 1321 Assignment 1 Answers: CN H H H H H

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Sara Yuen

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Download as PDF, TXT or read online on Scribd

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CHM 1321 Assignment 1 Answers

1) Draw Lewis structures, showing all unshared electrons, for the following covalent molecules: (a) CH3NH2 (b) CH2CH2 (c) C2H2
H H C N H H H
H H C C H H
H C C H

(d) CH3CH2CHO
H H O H C C C H H H

(e) CH3CH2OH2+
H H H C C O H H H H

(f) (CH3)3N
H H H C N C H H C H H H H

(g) CH3CN
H H C C N H

(h) CH3CH(OH)CH3
H H O H H C C C H H H H

(i) CH3NCO
H H C N C O H

(j) CH2CHCH(OH)CH2CO2H
H H H H O C C C C C H O H O H H

(k) NCCH2COCH2CHO
H O H O N C C C C C H H H

(l) CH3CH(CH3)CH2C(CH2CH3)2CHO
H H C H H C H H H H O H C C C C C H H C H H H H H C H H C H H

(m) (CH3)3C+
H H C H H H C C H H C H H

(n) CH3CH2OH H H C C O H H

(o) CH3CHCHCH2CHCHCOOH
H H H H H H O H C C C C C C C O H H H

(p) HC(O)N(CH3)2
O C H H C H N C H H H

2) There is a small portion of the periodic table that you must know to do organic chemistry. Construct this from memory including the group numbers, numbers of valence electrons, and electronegativities.
I H2.1 III IV V VI VIII

B2.0 C2.5 N3.0 O3.5 F4.0 Si1.8 P2.1 S2.5 Cl3.0 Br2.8 I2.6

Note: depending on the source you use, small differences exist between electronegativity values. Nevertheless, the relative values for electronegativity are always the same. 3) Draw structures for (a) Two compounds with the formula C4H10
CH3 H2 C H3C C H2 CH3 H3C CH CH3

Butane

2-methylpropane

(b) Three compounds with the formula C3H8O2 (There may be other structures, check with your TA if you are not sure)
OH HO C H2 H2 C C H2 OH HO C H2 CH CH 3 H 3C H2 C H C OH OH

1,3-propanediol
HO C H2 H2 C O CH3

1,2-propanediol
H3 C O H2 C O CH 3

1,1-propanediol

1,1-dimthoxymthane
O CH HO CH 3 CH 3 H 3C C H 3C OH OH

2-Mthoxythanol

1-Mthoxythanol

2,2-propanediol

(c) Two compounds with the formula C2H7N

H2 C H3C NH2 H3C H N CH3

ethylamine N,N-dimethylamine (d) Five compounds of formula C3H6O

O H2 C H3C C H OH C H2 H3C O H3C C CH3 OH H C C H O H2C H2C CH2 CH3 OH CH H2C OH H2C H2 C CH C CH3

Propanal
H C H2C

Propan-2-one

Prop-2-en-1-ol
H2C O

(E)-prop-1-en-1-ol

prop-1-en-2-ol

Oxacyclobutane

2-methyloxirane

Cyclopropanol

4) Name all the compounds in Question 3. Answers in Red. 5) Show the direction of the dipole moments of the following bonds. Use two methods. + + + + C Cl C H
C N C O

(a) C-Cl

(b) C-H

H
+

(d) C-O

+
C

(e) C-B

(f) N-H

(g) O-H

(h) C-Br

6) Draw the shape of s and p orbitals including phasing. Show the resulting shapes following sp, sp2 and sp3 hybridization.

sp2

sp3

7) For each molecule below: i. Draw complete molecular orbital structures using the LCAO method. ii. Label the atomic orbitals used to make the bonds (p, sp, sp2, sp3) iii. Label the bonds (, ). iv. Indicate the geometry of each atom (linear, trigonal planar, tetrahedral). (a) CH3CH2NH2 (b) CH3CO2H (c) CH3CHCHCH2CH3 (d) CH3NO2 (f) CH3OCH3

(e) CH3CN

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