NEED 100% CORRECT ANSWERS- ORGANIC CHEMISTRY COLLEGE LEVEL-TIP WILL BE GIVEN IF ALL ARE CORRECT!!

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CHAPTER10 - Practice Exercises 1. Name the following alkyl halides using IUPAC rules; a) CH3 - CH - CH - CH - CH - CH2 - CH3 CH3 CH3 Br b) CH3 c) I d) CH2 - CH2 - CH2 - CH2 - C C - CH2 Br Cl Br Br e) Cl 2. Draw structures corresponding to the following IUPAC names; a) 3- chloro- 2,2,4- trimethylhexane b) 4-Iodo- 3-ethyl-4-methylheptane c) trans- 1- chloro-2-methylcyclohexane c) ( R ) – 2 – chlorobutane e) ( 2R, 3S) – 2 –bromo –3- chlorobutane 3. Draw the resonance structures for the following species; a) b) c) 4. Rank the following compounds in each of the series in order of increasing oxidation level (1=lowest , 4=highest). a) CH3 - CH = CH –CH3 CH3 – CH2 – CH2 – CHO b) CH3 – CH2 – CH2 NH2 CH3 – CO – CH2 Cl CH3 – CH2 – CH = CH2 CH3 – CH2 – CH2 – COOH CH3 – CH2 – CH2 Br Br – CH2 – CH2 – CH2 - Cl 1 5. Complete the following reactions; a) monochlorination of 2-methylbutane b) NBS CH3 - CH2 - CH2 - CH = CH - CH3 c) CCl4 NBS d) CCl4 CH3 e) OH HBr CH3 ether f) SOCl2 NBS ether g) OH OH CCl4 PBr3 h) ether 1) Mg /ether Br i) 2) H2O NBS CCl4 j) ether CH3 - CH - CH2 - CH2 - CH2 Br + ( CH3CH2)2 Cu Li CH3 6. How would you prepare the following compounds, starting with cyclohexane or other compounds and other reagents. a) Bromocyclohexane b) Cyclohexene c) Cyclopropylcyclohexane d) Butylcyclopentane from cyclopentanol e) Butylcyclopentane from cyclpentane 7. Identify (tell) whether each of the following reactions is and OXIDATION or a REDUCTION; H O a) CH3 - C - OH CrO3 CH3 - C - CH3 NH3 b) O CH3 NH2 O c) 1) Mg / ether Br 2) H2O HBr /ether d) Br 2 8. Identify the missing letters , A, B, and C. a) CH3 - CH2 - CH - CH3 Mg ether Br H2O ?A 2Li b) CH3 CH2 CH2 CH2 Br ?B CH3CH2 Br CuI ?A ?B ?C ether pentane CH3 c) OH SOCl2 1) Mg /ether ?A ?B 2) H2O CH3 NBS ether d) 2 Li ?A CuI ?B ?C CH3CH2Br pentane 9. How many allylic and vinyllic hydrogen are in the following compounds; CH2 CH3 a) b) c) CH = CH2 d) e) f) CH2 3 CH3 - CH = CH - C CH 10. Identify the reagents a – d in the following reactions; Cl OH CH3 a) a CH3 b CH3 c CH3 CH3 Br b) a MgBr b c Br a c) Li b c d Cu Li 2 4

Tutor Answer

Geontiry
School: Boston College

Attached.

CHAPTER10 - Practice Exercises
Question 1
Name the following alkyl halides using IUPAC rules;
a) CH3 - CH - CH - CH - CH - CH2 - CH3
CH3 CH3 Br

b)

CH3

c)

I

d) CH2 - CH2 - CH2 - CH2 - C

C - CH2 Br

Cl
Br

Br

e)
Cl

ANSWERS
a) 4-Bromo-2,3,5-trimethylheptane
b) 2-Iodo-3-hexene
c) 3,5-Dibromo-2,4,6-trimethylheptane
d) 1-Bromo-7-chloro-2-heptyne
e) 3-Chlorocyclohexene
Question 2
Draw structures corresponding to the following IUPAC names;
a) 3- chloro- 2,2,4- trimethylhexane

b) 4-Iodo- 3-ethyl-4-methylheptane

c) trans- 1- chloro-2-methylcyclohexane

c) ( R ) – 2 – chlorobutane

e) ( 2R, 3S) – 2 –bromo –3- chlorobutane
ANSWERS
a) 3- chloro- 2,2,4- trimethylhexane

1

b) 4-Iodo- 3-ethyl-4-methylheptane

c) trans- 1- chloro-2-methylcyclohexane

c) ( R ) – 2 – chlorobutane

e) ( 2R, 3S) – 2 –bromo –3- chlorobutane

Question 3
Draw the resonance structures for the following species;

2

a)

b)

c)

ANSWERS
a)

b)

c)

Question 4
Rank the following compounds in each of the series in order of increasing oxidation level
(1=l...

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