ORG.CHEM:TXT+OWLV2+MINDTAP 6MTHS >BI<
ORG.CHEM:TXT+OWLV2+MINDTAP 6MTHS >BI<
8th Edition
ISBN: 9781337537612
Author: Brown
Publisher: CENGAGE L
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Chapter 10, Problem 10.16P

(a)

Interpretation Introduction

Interpretation:

Structural formula of the eachcompound has to be written.

Concept Introduction:

Nomenclature of Alcohol compounds:

The naming of theorganic compound is given by IUPAC (International Union for pure and applied chemistry). In the IUPAC names consist of certain rules for giving chemical names they are,

  • The longest chain of Carbon atoms containing the –OH group is the parent alkane and numbered from the end closer to –OH.
  • While naming the suffix ‘-e’ of the parent name is replaced with ‘-ol’ and the number is written to show the location of the –OH group.
  • For cyclic alcohols, numbering begins with the carbon bearing the –OH group; that no need to give its location a number. In complex alcohols, the number for the hydroxyl group is often placed between the infix and suffix. For example, 2-methylpropan-1-ol.
  • While numbering the longest carbon chain, the substituents should get least possible number.

(a)

Expert Solution
Check Mark

Explanation of Solution

Given name: Isopropylalcohol

In the given name, the alcohol indicates the presence of –OH group and the isopropyl indicates the longest carbon chain.

Therefore, the structure is,

ORG.CHEM:TXT+OWLV2+MINDTAP 6MTHS >BI<, Chapter 10, Problem 10.16P , additional homework tip  1

(b)

Interpretation Introduction

Interpretation:

Structural formula of the each compound has to be written.

Concept Introduction:

Nomenclature of saturated Alcohol compounds:

The naming of theorganic compound is given by IUPAC (International Union for pure and applied chemistry). In the IUPAC names consist of certain rules for giving chemical names they are,

  • The longest chain of Carbon atoms containing two –OH group is the parent alkane is named as diol and numbered from the end closer to –OH.
  • While naming the suffix ‘-e’ of the parent name is retained with ‘-ol’ and the number is written to show the location of the –OH group.
  • The presence of Carbon-carbon double bond is mentioned by changing the infix of the parent name from ‘-an’ to ‘-en’.
  • While numbering the longest carbon chain, the substituents should get least possible number.

(b)

Expert Solution
Check Mark

Explanation of Solution

Given name: Propyleneglycol

In the given name, the glycol indicates the presence of two –OH groups and two methylene carbons and the propylene indicates the longest carbon chain with a double bond.

Therefore, the structure is,

ORG.CHEM:TXT+OWLV2+MINDTAP 6MTHS >BI<, Chapter 10, Problem 10.16P , additional homework tip  2

(c)

Interpretation Introduction

Interpretation:

Structural formula of the each compound has to be written.

Concept Introduction:

Unsaturated Alcohol: Compounds containing –OH group and C=C groups are often referred to as unsaturated alcohols.

Nomenclature of unsaturated Alcohol compounds:

The naming of theorganic compound is given by IUPAC (International Union for pure and applied chemistry). In the IUPAC names consist of certain rules for giving chemical names they are,

  • The longest chain of Carbon atoms containing two –OH group is the parent alkane is named as diol and numbered from the end closer to –OH.
  • While naming the suffix ‘-e’ of the parent name is retained with ‘-ol’ and the number is written to show the location of the –OH group.
  • The presence of Carbon-carbon double bond is mentioned by changing the infix of the parent name from ‘-an’ to ‘-en’.
  • While numbering the longest carbon chain, the substituents should get least possible number.

(c)

Expert Solution
Check Mark

Explanation of Solution

Given name: 5-Methyl-2-hexanol

In the given compound, the longest carbon chain (2-hexanol) contains six carbons having –OH group located at C-2; and numbering the parent chain begins with carbon attached to the –OH group at C2, methyl substituent at C-5 is mentioned in prefix as ‘5-methyl’.

Therefore, the structure of the given compound is,

ORG.CHEM:TXT+OWLV2+MINDTAP 6MTHS >BI<, Chapter 10, Problem 10.16P , additional homework tip  3

(d)

Interpretation Introduction

Interpretation:

Structural formula of the each compound has to be written.

Concept Introduction:

Nomenclature of Alcohol compounds:

The naming of theorganic compound is given by IUPAC (International Union for pure and applied chemistry). In the IUPAC names consist of certain rules for giving chemical names they are,

  • The longest chain of Carbon atoms containing the –OH group is the parent alkane and numbered from the end closer to –OH.
  • While naming the suffix ‘-e’ of the parent name is replaced with ‘-ol’ and the number is written to show the location of the –OH group.
  • For cyclic alcohols, numbering begins with the carbon bearing the –OH group; that no need to give its location a number. In complex alcohols, the number for the hydroxyl group is often placed between the infix and suffix. For example, 2-methylpropan-1-ol.
  • While numbering the longest carbon chain, the substituents should get least possible number.

(d)

Expert Solution
Check Mark

Explanation of Solution

Given name: 2-Methyl-2-propyl-1,3-propanediol.

In the given compound, the longest carbon chain (1,3-propanediol) contains three carbons having –OH group located at C-1 and C-3; and numbering the parent chain begins with carbon attached to the –OH group at C1, both methyl and propyl substituents at C-2 is mentioned in prefix as ‘2-methyl-2-propyl’.

Therefore, the structure of the given compound is,

ORG.CHEM:TXT+OWLV2+MINDTAP 6MTHS >BI<, Chapter 10, Problem 10.16P , additional homework tip  4

(e)

Interpretation Introduction

Interpretation:

Structural formula of the each compound has to be written.

Concept Introduction:

Unsaturated Alcohol: Compounds containing –OH group and C=C groups are often referred to as unsaturated alcohols.

Nomenclature of unsaturated Alcohol compounds:

The naming of theorganic compound is given by IUPAC (International Union for pure and applied chemistry). In the IUPAC names consist of certain rules for giving chemical names they are,

  • The longest chain of Carbon atoms containing two –OH group is the parent alkane is named as diol and numbered from the end closer to –OH.
  • While naming the suffix ‘-e’ of the parent name is retained with ‘-ol’ and the number is written to show the location of the –OH group.
  • The presence of Carbon-carbon double bond is mentioned by changing the infix of the parent name from ‘-an’ to ‘-en’.
  • While numbering the longest carbon chain, the substituents should get least possible number.

(e)

Expert Solution
Check Mark

Explanation of Solution

Given name: 1-chloro-2-hexanol

In the given compound, the longest carbon chain (2-hexanol) contains six carbons having –OH group located at C-2; and numbering the longest parent chain, Chloro substituentlocated at C-1 is mentioned in prefix as ‘1-chloro-’.

Therefore, the structure of the given compound is,

ORG.CHEM:TXT+OWLV2+MINDTAP 6MTHS >BI<, Chapter 10, Problem 10.16P , additional homework tip  5

(f)

Interpretation Introduction

Interpretation:

Structural formula of the each compound has to be written.

Concept Introduction:

Nomenclature of Alcohol compounds:

The naming of theorganic compound is given by IUPAC (International Union for pure and applied chemistry). In the IUPAC names consist of certain rules for giving chemical names they are,

  • The longest chain of Carbon atoms containing the –OH group is the parent alkane and numbered from the end closer to –OH.
  • While naming the suffix ‘-e’ of the parent name is replaced with ‘-ol’ and the number is written to show the location of the –OH group.
  • For cyclic alcohols, numbering begins with the carbon bearing the –OH group; that no need to give its location a number. In complex alcohols, the number for the hydroxyl group is often placed between the infix and suffix. For example, 2-methylpropan-1-ol.
  • While numbering the longest carbon chain, the substituents should get least possible number.

(f)

Expert Solution
Check Mark

Explanation of Solution

Given name: cis-3-Isobutylcyclohexanol

In the given compound, the longest carbon cyclic ring (cyclohexanol) contains six carbons having –OH group located at C-1; and numbering the longest parent ring, Isobutyl substituent located at C-3 is mentioned in prefix as ‘3-isobutyl-’. The ‘cis’ term indicates two substituents –OH and isobutyl on the same side.

Therefore, the structure of the given compound is,

ORG.CHEM:TXT+OWLV2+MINDTAP 6MTHS >BI<, Chapter 10, Problem 10.16P , additional homework tip  6

(g)

Interpretation Introduction

Interpretation:

Structural formula of the each compound has to be written.

Concept Introduction:

Unsaturated Alcohol: Compounds containing –OH group and C=C groups are often referred to as unsaturated alcohols.

Nomenclature of unsaturated Alcohol compounds:

The naming of theorganic compound is given by IUPAC (International Union for pure and applied chemistry). In the IUPAC names consist of certain rules for giving chemical names they are,

  • The longest chain of Carbon atoms containing two –OH group is the parent alkane is named as diol and numbered from the end closer to –OH.
  • While naming the suffix ‘-e’ of the parent name is retained with ‘-ol’ and the number is written to show the location of the –OH group.
  • The presence of Carbon-carbon double bond is mentioned by changing the infix of the parent name from ‘-an’ to ‘-en’.
  • While numbering the longest carbon chain, the substituents should get least possible number.

(g)

Expert Solution
Check Mark

Explanation of Solution

Given name: 2,2-Dimethyl-1-propanol

In the given compound, the longest carbon chain (1-propanol) contains three carbons having –OH group located at C-1; and numbering the longest parent chain, two methyl substituents located at C-2 is mentioned in prefix as ‘2,2-Dimethyl-’.

Therefore, the structure of the given compound is,

ORG.CHEM:TXT+OWLV2+MINDTAP 6MTHS >BI<, Chapter 10, Problem 10.16P , additional homework tip  7

(h)

Interpretation Introduction

Interpretation:

Structural formula of the each compound has to be written.

Concept Introduction:

Nomenclature of saturated Alcohol compounds:

The naming of theorganic compound is given by IUPAC (International Union for pure and applied chemistry). In the IUPAC names consist of certain rules for giving chemical names they are,

  • The longest chain of Carbon atoms containing two –OH group is the parent alkane is named as diol and numbered from the end closer to –OH.
  • While naming the suffix ‘-e’ of the parent name is retained with ‘-ol’ and the number is written to show the location of the –OH group.
  • The presence of Carbon-carbon double bond is mentioned by changing the infix of the parent name from ‘-an’ to ‘-en’.
  • While numbering the longest carbon chain, the substituents should get least possible number.

(h)

Expert Solution
Check Mark

Explanation of Solution

Given name: 2-Mercaptoethanol

In the given compound, the longest carbon chain (ethanol) contains two carbons having –OH group located at C-1; and numbering the longest parent chain, mercapto substituents (-SH) located at C-2 is mentioned in prefix as ‘2-Mercapto-’.

Therefore, the structure of the given compound is,

ORG.CHEM:TXT+OWLV2+MINDTAP 6MTHS >BI<, Chapter 10, Problem 10.16P , additional homework tip  8

(i)

Interpretation Introduction

Interpretation:

Structural formula of the each compound has to be written.

Concept Introduction:

Nomenclature of saturated Alcohol compounds:

The naming of theorganic compound is given by IUPAC (International Union for pure and applied chemistry). In the IUPAC names consist of certain rules for giving chemical names they are,

  • The longest chain of Carbon atoms containing two –OH group is the parent alkane is named as diol and numbered from the end closer to –OH.
  • While naming the suffix ‘-e’ of the parent name is retained with ‘-ol’ and the number is written to show the location of the –OH group.
  • The presence of Carbon-carbon double bond is mentioned by changing the infix of the parent name from ‘-an’ to ‘-en’.
  • While numbering the longest carbon chain, the substituents should get least possible number.

(i)

Expert Solution
Check Mark

Explanation of Solution

Given name: Allyl alcohol

In the given compound, the longest carbon chain (allyl) contains three carbons having –OH group located at C-1while numbering the longest parent chain and a double bond at C-2.

Therefore, the structure of the given compound is,

ORG.CHEM:TXT+OWLV2+MINDTAP 6MTHS >BI<, Chapter 10, Problem 10.16P , additional homework tip  9

(j)

Interpretation Introduction

Interpretation:

Structural formula of the each compound has to be written.

Concept Introduction:

Nomenclature of saturated Alcohol compounds:

The naming of theorganic compound is given by IUPAC (International Union for pure and applied chemistry). In the IUPAC names consist of certain rules for giving chemical names they are,

  • The longest chain of Carbon atoms containing two –OH group is the parent alkane is named as diol and numbered from the end closer to –OH.
  • While naming the suffix ‘-e’ of the parent name is retained with ‘-ol’ and the number is written to show the location of the –OH group.
  • The presence of Carbon-carbon double bond is mentioned by changing the infix of the parent name from ‘-an’ to ‘-en’.
  • While numbering the longest carbon chain, the substituents should get least possible number.

(j)

Expert Solution
Check Mark

Explanation of Solution

Given name: trans-2-vinylcyclohexanol

In the given compound, the longest carbon cyclic ring (cyclohexanol) contains six carbons having –OH group located at C-1; and numbering the longest parent ring, vinyl substituent located at C-2 is mentioned in prefix as ‘2-vinyl-’. The ‘trans’ term indicates two substituents OH and vinyl on the opposite side.

Therefore, the structure of the given compound is,

ORG.CHEM:TXT+OWLV2+MINDTAP 6MTHS >BI<, Chapter 10, Problem 10.16P , additional homework tip  10

(k)

Interpretation Introduction

Interpretation:

Structural formula of the each compound has to be written.

Concept Introduction:

Nomenclature of Alcohol compounds:

The naming of theorganic compound is given by IUPAC (International Union for pure and applied chemistry). In the IUPAC names consist of certain rules for giving chemical names they are,

  • The longest chain of Carbon atoms containing the –OH group is the parent alkane and numbered from the end closer to –OH.
  • While naming the suffix ‘-e’ of the parent name is replaced with ‘-ol’ and the number is written to show the location of the –OH group.
  • For cyclic alcohols, numbering begins with the carbon bearing the –OH group; that no need to give its location a number. In complex alcohols, the number for the hydroxyl group is often placed between the infix and suffix. For example, 2-methylpropan-1-ol.
  • While numbering the longest carbon chain, the substituents should get least possible number.

(k)

Expert Solution
Check Mark

Explanation of Solution

Given name: (Z)-5-Methyl-2-hexen-1-ol

In the given compound, the longest carbon chain (2-hexen-1-ol) contains six carbons having –OH group located at C-2 and a double bond located at C-2; and numbering the longest parent chain, Methyl substituent located at C-5 is mentioned in prefix as ‘5-methyl-’. The term (Z) indicates the –OH and methyl groups are locate on same side of the double bond.

Therefore, the structure of the given compound is,

ORG.CHEM:TXT+OWLV2+MINDTAP 6MTHS >BI<, Chapter 10, Problem 10.16P , additional homework tip  11

(l)

Interpretation Introduction

Interpretation:

Structural formula of the each compound has to be written.

Concept Introduction:

Nomenclature of Alcohol compounds:

The naming of theorganic compound is given by IUPAC (International Union for pure and applied chemistry). In the IUPAC names consist of certain rules for giving chemical names they are,

  • The longest chain of Carbon atoms containing the –OH group is the parent alkane and numbered from the end closer to –OH.
  • While naming the suffix ‘-e’ of the parent name is replaced with ‘-ol’ and the number is written to show the location of the –OH group.
  • For cyclic alcohols, numbering begins with the carbon bearing the –OH group; that no need to give its location a number. In complex alcohols, the number for the hydroxyl group is often placed between the infix and suffix. For example, 2-methylpropan-1-ol.
  • While numbering the longest carbon chain, the substituents should get least possible number.

(l)

Expert Solution
Check Mark

Explanation of Solution

Given name: 2-Propyn-1-ol

In the given compound, the longest carbon chain (2-propyn-1-ol) contains three carbons having –OH group located at C-1 and a triple bond located at C-2 while numbering the longest parent chain.

Therefore, the structure of the given compound is,

ORG.CHEM:TXT+OWLV2+MINDTAP 6MTHS >BI<, Chapter 10, Problem 10.16P , additional homework tip  12

(m)

Interpretation Introduction

Interpretation:

Structural formula of the each compound has to be written.

Concept Introduction:

Nomenclature of Alcohol compounds:

The naming of theorganic compound is given by IUPAC (International Union for pure and applied chemistry). In the IUPAC names consist of certain rules for giving chemical names they are,

  • The longest chain of Carbon atoms containing the –OH group is the parent alkane and numbered from the end closer to –OH.
  • While naming the suffix ‘-e’ of the parent name is replaced with ‘-ol’ and the number is written to show the location of the –OH group.
  • For cyclic alcohols, numbering begins with the carbon bearing the –OH group; that no need to give its location a number. In complex alcohols, the number for the hydroxyl group is often placed between the infix and suffix. For example, 2-methylpropan-1-ol.
  • While numbering the longest carbon chain, the substituents should get least possible number.

(m)

Expert Solution
Check Mark

Explanation of Solution

Given name: 3-Chloro-1,2-propandiol

In the given compound, the longest carbon chain (1,2-propandiol) contains three carbons having –OH group located at C-1 and C-2 and numbering the longest parent chain, Chloro substituent located at C-3 is mentioned in prefix as ‘3-Chloro-’.

Therefore, the structure of the given compound is,

ORG.CHEM:TXT+OWLV2+MINDTAP 6MTHS >BI<, Chapter 10, Problem 10.16P , additional homework tip  13

(n)

Interpretation Introduction

Interpretation:

Structural formula of the each compound has to be written.

Concept Introduction:

Nomenclature of Alcohol compounds:

The naming of theorganic compound is given by IUPAC (International Union for pure and applied chemistry). In the IUPAC names consist of certain rules for giving chemical names they are,

  • The longest chain of Carbon atoms containing the –OH group is the parent alkane and numbered from the end closer to –OH.
  • While naming the suffix ‘-e’ of the parent name is replaced with ‘-ol’ and the number is written to show the location of the –OH group.
  • For cyclic alcohols, numbering begins with the carbon bearing the –OH group; that no need to give its location a number. In complex alcohols, the number for the hydroxyl group is often placed between the infix and suffix. For example, 2-methylpropan-1-ol.
  • While numbering the longest carbon chain, the substituents should get least possible number.

(n)

Expert Solution
Check Mark

Explanation of Solution

Given name: cis-3-Pentene-1-ol

In the given compound, the longest carbon chain (3-penten-1-ol) contains five carbons having –OH group located at C-1and a double bond located at C-3 while numbering the longest parent chain. The term (cis) indicates two Hydrogen atoms are locate on same side of the double bond.

Therefore, the structure of the given compound is,

ORG.CHEM:TXT+OWLV2+MINDTAP 6MTHS >BI<, Chapter 10, Problem 10.16P , additional homework tip  14

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Chapter 10 Solutions

ORG.CHEM:TXT+OWLV2+MINDTAP 6MTHS >BI<

Ch. 10.7 - Prob. AQCh. 10.7 - Prob. BQCh. 10.7 - Prob. CQCh. 10.7 - Prob. DQCh. 10.7 - Which step in the reaction would you expect to be...Ch. 10.7 - Prob. FQCh. 10.7 - Prob. GQCh. 10.8 - Prob. 10.11PCh. 10.8 - Prob. AQCh. 10.8 - Prob. BQCh. 10.8 - Prob. CQCh. 10.8 - Why does nature use a reagent as complex as NAD+...Ch. 10.8 - -Hydroxyketones and -hydroxyaldehydes are also...Ch. 10.9 - Write IUPAC names for these thiols.Ch. 10 - Which are secondary alcohols?Ch. 10 - Name each compound.Ch. 10 - Prob. 10.16PCh. 10 - Name and draw structural formulas for the eight...Ch. 10 - Arrange these compounds in order of increasing...Ch. 10 - Arrange these compounds in order of increasing...Ch. 10 - Prob. 10.20PCh. 10 - Prob. 10.21PCh. 10 - Arrange the compounds in each set in order of...Ch. 10 - Prob. 10.23PCh. 10 - The decalinols A and B can be equilibrated using...Ch. 10 - Prob. 10.25PCh. 10 - Select the stronger acid from each pair and...Ch. 10 - Prob. 10.27PCh. 10 - In each equilibrium, label the stronger acid, the...Ch. 10 - Write equations for the reaction of 1-butanol with...Ch. 10 - Write equations for the reaction of 2-butanol with...Ch. 10 - Prob. 10.31PCh. 10 - When (R)-2-butanol is left standing in aqueous...Ch. 10 - Two diastereomeric sets of enantiomers, A/B and...Ch. 10 - Acid-catalyzed dehydration of 3-methyl-2-butanol...Ch. 10 - Show how you might bring about the following...Ch. 10 - Propose a mechanism for the following pinacol...Ch. 10 - Prob. 10.37PCh. 10 - Show how each alcohol or diol can be prepared from...Ch. 10 - Dihydropyran is synthesized by treating...Ch. 10 - Show how to convert propene to each of these...Ch. 10 - Prob. 10.41PCh. 10 - Prob. 10.42PCh. 10 - The tosylate of a primary alcohol normally...Ch. 10 - Prob. 10.44PCh. 10 - Show how to convert cyclohexene to each compound...Ch. 10 - Prob. 10.46PCh. 10 - Ethanol (CH3CH2OH) and dimethyl ether (CH3OCH3)...Ch. 10 - Prob. 10.48PCh. 10 - Prob. 10.49PCh. 10 - Prob. 10.50PCh. 10 - Write the products of the following sequences of...Ch. 10 - Alcohols are important for organic synthesis,...Ch. 10 - Using your reaction roadmap as a guide, show how...Ch. 10 - Using your reaction roadmap as a guide, show how...Ch. 10 - Using your reaction roadmap as a guide, show how...Ch. 10 - Using your reaction roadmap as a guide, show how...Ch. 10 - Prob. 10.57PCh. 10 - Prob. 10.58PCh. 10 - Prob. 10.59P
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