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Organic Chemistry Exam Prep: Nomenclature, Stereochemistry, SN1/SN2 & Elimination, Schemes and Mind Maps of Organic Chemistry

Syracuse UniversityOrganic Chemistry

A comprehensive set of practice problems for organic chemistry, covering key concepts such as nomenclature, stereochemistry, sn1/sn2 reactions, and elimination reactions. It includes multiple-choice questions, reaction mechanisms, and detailed explanations, making it an excellent resource for students preparing for exams or seeking to solidify their understanding of these fundamental topics.

Typology: Schemes and Mind Maps

2023/2024

Uploaded on 11/18/2024

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stephanie-amaro-1 🇺🇸

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Friday Afternoon Challenge
Friday, November 1, 2024
Note Exam 2 will be Wednesday, November 6, 2024
1. 1. (Nomenclature) Give acceptable IUPAC name for each of the compounds below. Be sure
to indicate the stereochemistry (e.g. cis or trans, R or S, E or Z) where appropriate:
a.
b.
c.
d.
e.
HO H
H3C
CH3
Br
S
s2hexano
v
Rs shept 5ene 30
c
ss6ethyl 5fluoro 2methyl
octane
43
s
cite 4methyl cyclohex 2ene so
Z2bromo 2butene
00
pf3
pf4
pf5

Partial preview of the text

Download Organic Chemistry Exam Prep: Nomenclature, Stereochemistry, SN1/SN2 & Elimination and more Schemes and Mind Maps Organic Chemistry in PDF only on Docsity!

Friday Afternoon Challenge Friday, November 1, 2024 Note Exam 2 will be Wednesday, November 6, 2024

    1. (Nomenclature) Give acceptable IUPAC name for each of the compounds below. Be sure to indicate the stereochemistry (e.g. cis or trans, R or S, E or Z) where appropriate: a. b. c. d. e. HO H H 3 C CH 3 Br

S

s (^2) hexano v

Rs

s (^) hept 5 ene^3 c s s^6 ethyl^ 5 fluoro^ 2 methyl octane 43

s

cite

4 methyl cyclohex 2 ene^

s o

Z 2 bromo^ 2 butene

f. g. h.

  1. Assign absolute configuration as R or S with two chiral carbons below:
  2. Rank following compounds with respect to SN1 reactivity. (least reactive = 1, most reactive= 3) a. Br OH H 3 C CH 3 Br H 3 C (^) CH 3 Cis 2 bromo cyclohexane

H

cis 2 butene trans 2 buten

00H

s A Soit 2 EPH S f s 3

i

3 2 1 Correction

a. Draw the structures for each intermediate I through VII b. Draw the carbocation that is formed in this reaction. c. What is the rate determining step? d. Is the overall reaction endothermic or exothermic? e. What type of reaction is this (SN1, SN2, E1, or E2). Explain your reasoning.

  1. Which molecule below would undergo a hydride shift in an E1 reaction with H 2 SO 4? a. 1 - methyl cyclohexanol b. 2 - methyl cyclohexanol c. 3 - methyl cyclohexanol 1 Reactants 2H I carbocation I
s

8th F iii F I it products Carbocation Formation Exothermic

c

carbocation

formatio

Snl (^) bEtti.it 7ao^ d Batedependsonlyon sab Essifts out IF D (^) IEEE 11 I 1

O- Br

  1. A second order elimination (E2) reaction is a bimolecular reaction, and its rate is dependent on the concentration of substrate and base. a. What basses favor the Zaitsev Product formation in an E2 reaction? b. What basses favor the Hofmann Product formation in an E2 reaction? Draw the two products expected in the following reactions. Identify the expected major and minor products. c. d. e. f. g. Cl O- Cl (^) CH 3 O- Br CH 3 O- O- Br Small (^) strong Base CH 300 StrongBulky^ Base 100 Bulky minor major

major

minor major minor IF minor major

minor

major

(e) (f)

  1. Show by writing a suitable series of equations how you could 2-methyl- 2 - butene from the starting material, 2 - chloro- 2 - methylbutane, and any necessary organic or inorganic reagents. (Hint: E1 mechanism for dehydrohalogenation)
  2. Provide a clear mechanism to explain the formation of the product shown. Use curved arrows to indicate “electron flow”. Remember to show only one step at a time. Show all intermediates and all formal charges. OH E mild

X

Is

N

Pr

BE

M Ex