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Introduction to Organic Chemistry Exam 1 Key - Summer 2006 - Prof. Clarke W. Earley, Exams of Organic Chemistry

The answers to exam 1 for the introduction to organic chemistry course during the summer 2006 semester. It includes questions related to formal charge, geometry, drawing structures, hydrocarbons, isomers, and organic reactions.

Typology: Exams

Pre 2010

Uploaded on 08/01/2009

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CHEM 10052 - Introduction to Organic Chemistry - Summer 2006
Exam #1 Key - 100 Points
1. [5 pts] (10.15)
CC
H
H
H
C C
C
C
H
H C H
: O :
2. [6 pts] (10.47) δ+and δ.
3. [4 pts] (–) Formal charge.
4. [4 pts] (10.21) Geometry.
δ+
δ+
δ+
δ
δ
δ
δ
N
C
C
C
H
H H
H
C
: O : O :
..
..
N
..
−1 Formal Charge
+1 Formal Charge
Trigonal Planar
Tetrahedral
5. [6 pts] (11.13) Draw structures.
(a) 2-ethyl-4,4-dimethylpentane =
(b) 3-isopropyl-1,1-dimethylcyclohexane =
6. [3 pts] (11.23)
= 2,2,4-trimethylhexane
7. [3 pts] (11.13) Condensed formula =
CH3CH(CH3)CH2C(CH3)2CH3
or
CH3CH(CH3)CH2C(CH3)3
8. [3 pts] (11.13) Stick structure =
9. [6 pts] (11.55) Hydrocarbons
(a) Neither is water soluble
(b) Both are flammable (burn)
(c) Alkenes more reactive ?
10. [4 pts] (11.19) Compare
(a) Different formulas (C5H12 vs. CH4)
(b) Isomers (2,3-dimethylpentane vs.
2,4-dimethylpentane)
11. [6 pts] (11.31)
12. [4 pts] (11.52) Carbon atoms in primary chain
(a) 7
(b) 7
13. [6 pts] # H’s =
O
O
1
1
3
14. [2 pts] Most stable =
CH3
H3C
CH3
equatorial equatorial
equatorial
15. [6 pts] (12.23) Isomers
(a) =cis
(b)
H3C
H3C CH3
CC
H
= Neither
(c)
CH3
H3C
=cis
pf2

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CHEM 10052 - Introduction to Organic Chemistry - Summer 2006

Exam #1 Key - 100 Points

  1. [5 pts] (10.15)

C C

H H

H C C

C

C

H

H C H : O :

  1. [6 pts] (10.47) δ+^ and δ−.
  2. [4 pts] (–) Formal charge.
  3. [4 pts] (10.21) Geometry.

δ+ δ+

δ+

δ−

δ−^ δ−

δ−

N C

H C C

H H

H

: O (^) C : O : .. ..

N..

−1 Formal Charge

+1 Formal ChargeTrigonal Planar

Tetrahedral

  1. [6 pts] (11.13) Draw structures. (a) 2-ethyl-4,4-dimethylpentane =

(b) 3-isopropyl-1,1-dimethylcyclohexane =

  1. [3 pts] (11.23)

= 2,2,4-trimethylhexane

  1. [3 pts] (11.13) Condensed formula = CH 3 CH(CH 3 )CH 2 C(CH 3 ) 2 CH 3 or CH 3 CH(CH 3 )CH 2 C(CH 3 ) 3
  2. [3 pts] (11.13) Stick structure =
    1. [6 pts] (11.55) Hydrocarbons (a) Neither is water soluble (b) Both are flammable (burn) (c) Alkenes more reactive?
  3. [4 pts] (11.19) Compare (a) Different formulas (C 5 H 12 vs. CH 4 ) (b) Isomers (2,3-dimethylpentane vs. 2,4-dimethylpentane)
  4. [6 pts] (11.31)
  5. [4 pts] (11.52) Carbon atoms in primary chain (a) 7 (b) 7
  6. [6 pts] # H’s = O

O

1 1

3

  1. [2 pts] Most stable = H 3 C CH 3

CH 3

equatorial equatorial

equatorial

  1. [6 pts] (12.23) Isomers (a) = cis

(b)

H 3 C H 3 C CH 3

C C

H = Neither

(c)

H 3 C CH 3 = cis

Dr. Earley CHEM 10052 - Introduction to Organic Chemistry Summer 2006

  1. [8 pts] (11.37, 11.55) Correct choices. Property Tested water hexane 1-hexene Soluble in water? – No No Burns? No Yes Yes Reacts with HCl? – No Yes
  2. [12 pts] (12.34) Organic products

(a) GGGHGG^2 GA

Pt

(b) GGGHBrGGGGGA Br

(c)

CH 3

H Br 2

GGGGGGGA

CH 3 Br Br H

(d)

CH 3

H GGG^ HGG^2 GOGGA

H 2 SO 4

CH 3 OH

  1. [4 pts] (11.40) 2 C 4 H 10 + 13 O 2 −→ 8 CO 2 + 10 H 2 O
  2. [2 pts] (12.39, 12.41) Prepare 2-bromobutane with (d) [ a & c ]
  3. [2 pts] (12.39, 12.41) Prepare 2-bromo-3-methylbutane with (c)
  4. [4 pts] (12.57) Terpene units