Organic Chemistry (9th Edition)
Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
Question
Book Icon
Chapter 8.6, Problem 8.9P

(a)

Interpretation Introduction

To determine: The conversion of but1ene into 2methoxybutane.

Interpretation: The conversion of the given reactions is to be stated.

Concept introduction: Oxymercuration-demercuration is one of the methods used to convert alkenes into alcohols. This type of reaction follows Markovinokov’s rule.

According to Markovnikov’s rule, the positive part of acid gets attached to that carbon atom in C=C bond which carries maximum number of hydrogen atoms and the negative part of acid gets attached to that carbon atom in C=C bond which has minimum number of hydrogen atoms.

(b)

Interpretation Introduction

To determine: The conversion of 1iodo2methylcyclopentane into 1methylcyclopentanol.

Interpretation: The conversion of the given reactions is to be stated.

Concept introduction: The general steps followed by Oxymercuration-demercuration reaction are stated below:

  • Formation of mercurinium ion.
  • Attack of water on mercurinium ion to give alcohol.
  • Demercuration

(c)

Interpretation Introduction

To determine: The conversion of 3methylpent1ene into 3methylpentan2ol.

Interpretation: The conversion of the given reactions is to be stated.

Concept introduction: Oxymercuration-demercuration is one of the methods used to convert alkenes into alcohols. This type of reaction follows Markovinokov’s rule.

According to Markovnikov’s rule, the positive part of acid gets attached to that carbon atom in C=C bond which carries maximum number of hydrogen atoms and the negative part of acid will attach to that carbon atom in C=C bond which has minimum number of hydrogen atoms.

The general steps followed by Oxymercuration-demercuration reaction are stated below:

  • Formation of mercurinium ion.
  • Attack of water on mercurinium ion to give alcohol.
  • Demercuration

Blurred answer
Students have asked these similar questions
2. Name each alkyne. a. CH3CH₂CH₂C=CH b. CH3CH₂CH₂C=CCH3 3. Predict the product of the following reactions. a. CH = CCH3 + HCI b. CH CCH₂CH3 + O2
Draw the products obtained from the SN2 reaction of a. 2-bromobutane and methoxide ion.          b. (R)-2-bromobutane and methoxide ion. c. (S)-3-chlorohexane and hydroxide ion. d. 3-iodopentane and hydroxide ion.
Draw the organic products formed when cyclopentene is treated with each reagent. With some reagents, no reaction occurs. a.H2 + Pd-C b.H2 + Lindlar catalyst c.Na, NH3 d.CH3CO3H e.[1] CH3CO3H; [2] H2O, HO− f.[1]OsO4 + NMO; [2] NaHSO3, H2O g.KMnO4, H2O, HO− h.[1] LiAlH4; [2] H2O i. [1] O3; [2] CH3SCH3 j.(CH3)3COOH, Ti[OCH(CH3)2]4, (−)-DET k.mCPBA l.Product in (k); then [1] LiAlH4; [2] H2O

Chapter 8 Solutions

Organic Chemistry (9th Edition)

Ch. 8.7A - Prob. 8.11PCh. 8.7C - Prob. 8.12PCh. 8.7C - Prob. 8.13PCh. 8.7C - a. When (Z)-3-methylhex-3-ene undergoes...Ch. 8.7C - Prob. 8.15PCh. 8.7C - Prob. 8.16PCh. 8.8B - Prob. 8.17PCh. 8.8B - Prob. 8.18PCh. 8.9 - Prob. 8.19PCh. 8.9 - Prob. 8.20PCh. 8.9 - Prob. 8.21PCh. 8.9 - Prob. 8.22PCh. 8.10 - Prob. 8.23PCh. 8.10 - Prob. 8.24PCh. 8.10 - Prob. 8.25PCh. 8.11A - Prob. 8.26PCh. 8.11B - Prob. 8.27PCh. 8.11B - Prob. 8.28PCh. 8.12 - Prob. 8.29PCh. 8.13 - a. Propose a mechanism for the conversion of...Ch. 8.13 - Magnesium monoperoxyphthalate (MMPP) epoxidizes...Ch. 8.13 - Predict the major products of the following...Ch. 8.13 - When 1,2-epoxycyclohexane (cyclohexene oxide) is...Ch. 8.14C - Predict the major products of the following...Ch. 8.14C - Prob. 8.35PCh. 8.15B - Prob. 8.36PCh. 8.15C - Predict the major products of the following...Ch. 8.16A - Prob. 8.38PCh. 8.16A - Prob. 8.39PCh. 8.16B - Prob. 8.40PCh. 8.16B - Prob. 8.41PCh. 8.16C - Prob. 8.42PCh. 8.17B - Prob. 8.43PCh. 8.17B - Prob. 8.44PCh. 8.17B - Show how you would synthesize each compound,...Ch. 8 - Prob. 8.46SPCh. 8 - Prob. 8.47SPCh. 8 - Give the products expected when the following...Ch. 8 - Show how you would make the following compounds...Ch. 8 - Using 1,2-dimethylcyclohexene as your starting...Ch. 8 - Show how you would synthesize each compound using...Ch. 8 - Prob. 8.52SPCh. 8 - Show how you might use olefin metathesis to...Ch. 8 - Prob. 8.54SPCh. 8 - Prob. 8.55SPCh. 8 - Propose mechanisms consistent with the following...Ch. 8 - Prob. 8.57SPCh. 8 - Prob. 8.58SPCh. 8 - Draw a reaction-energy diagram for the propagation...Ch. 8 - Prob. 8.60SPCh. 8 - Prob. 8.61SPCh. 8 - Prob. 8.62SPCh. 8 - Prob. 8.63SPCh. 8 - Prob. 8.64SPCh. 8 - Prob. 8.65SPCh. 8 - Prob. 8.66SPCh. 8 - Prob. 8.67SPCh. 8 - Prob. 8.68SPCh. 8 - Prob. 8.69SPCh. 8 - Prob. 8.70SPCh. 8 - Prob. 8.71SPCh. 8 - Prob. 8.72SPCh. 8 - Prob. 8.73SPCh. 8 - Prob. 8.74SPCh. 8 - Prob. 8.75SPCh. 8 - Prob. 8.76SPCh. 8 - Prob. 8.77SPCh. 8 - Prob. 8.78SPCh. 8 - Prob. 8.79SP
Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning