The expected reactant that can yield 1-decanol as product of NaBH 4 reduction should be formulated. Concept introduction: The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below. Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below; Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

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Answer 1

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Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 8.5, Problem 8.10E

(a)

Interpretation Introduction

Interpretation: The expected reactant that can yield 1-decanol as product of NaBH4 reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below;

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

(b)

Interpretation Introduction

Interpretation:The expected reactant that can yield 4-methyl-2-pentanol as product of NaBH4 reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below;

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

(c)

Interpretation Introduction

Interpretation:The expected reactant that can yield cyclopentylmethanol asproduct of NaBH4 reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below;

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

(d)

Interpretation Introduction

Interpretation:The expected reactant that can yield 1,4-cyclohexanediol as product of NaBH4 reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below;

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

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Answer 2

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Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 8.5, Problem 8.10E

(a)

Interpretation Introduction

Interpretation: The expected reactant that can yield 1-decanol as product of NaBH4 reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below;

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

(b)

Interpretation Introduction

Interpretation:The expected reactant that can yield 4-methyl-2-pentanol as product of NaBH4 reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below;

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

(c)

Interpretation Introduction

Interpretation:The expected reactant that can yield cyclopentylmethanol asproduct of NaBH4 reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below;

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

(d)

Interpretation Introduction

Interpretation:The expected reactant that can yield 1,4-cyclohexanediol as product of NaBH4 reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below;

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

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Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 8.5, Problem 8.10E

(a)

Interpretation Introduction

Interpretation: The expected reactant that can yield 1-decanol as product of NaBH4 reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below;

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

(b)

Interpretation Introduction

Interpretation:The expected reactant that can yield 4-methyl-2-pentanol as product of NaBH4 reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below;

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

(c)

Interpretation Introduction

Interpretation:The expected reactant that can yield cyclopentylmethanol asproduct of NaBH4 reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below;

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

(d)

Interpretation Introduction

Interpretation:The expected reactant that can yield 1,4-cyclohexanediol as product of NaBH4 reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below;

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

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Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 8.5, Problem 8.10E

(a)

Interpretation Introduction

Interpretation: The expected reactant that can yield 1-decanol as product of NaBH4 reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below;

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

(b)

Interpretation Introduction

Interpretation:The expected reactant that can yield 4-methyl-2-pentanol as product of NaBH4 reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below;

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

(c)

Interpretation Introduction

Interpretation:The expected reactant that can yield cyclopentylmethanol asproduct of NaBH4 reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below;

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

(d)

Interpretation Introduction

Interpretation:The expected reactant that can yield 1,4-cyclohexanediol as product of NaBH4 reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below;

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

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Answer 5

Chapter 8.5, Problem 8.10E

(a)

Interpretation Introduction

Interpretation: The expected reactant that can yield 1-decanol as product of NaBH4 reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below;

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

(b)

Interpretation Introduction

Interpretation:The expected reactant that can yield 4-methyl-2-pentanol as product of NaBH4 reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below;

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

(c)

Interpretation Introduction

Interpretation:The expected reactant that can yield cyclopentylmethanol asproduct of NaBH4 reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below;

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

(d)

Interpretation Introduction

Interpretation:The expected reactant that can yield 1,4-cyclohexanediol as product of NaBH4 reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below;

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

Answer 6

Chapter 8.5, Problem 8.10E

(a)

Interpretation Introduction

Interpretation: The expected reactant that can yield 1-decanol as product of NaBH4 reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below;

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

Answer 7

Chapter 8.5, Problem 8.10E

(a)

Interpretation Introduction

Interpretation: The expected reactant that can yield 1-decanol as product of NaBH4 reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below;

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

Answer 8

(b)

Interpretation Introduction

Interpretation:The expected reactant that can yield 4-methyl-2-pentanol as product of NaBH4 reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below;

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

Answer 9

(b)

Interpretation Introduction

Interpretation:The expected reactant that can yield 4-methyl-2-pentanol as product of NaBH4 reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below;

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

Answer 10

(c)

Interpretation Introduction

Interpretation:The expected reactant that can yield cyclopentylmethanol asproduct of NaBH4 reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below;

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

Answer 11

(c)

Interpretation Introduction

Interpretation:The expected reactant that can yield cyclopentylmethanol asproduct of NaBH4 reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below;

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

Answer 12

(d)

Interpretation Introduction

Interpretation:The expected reactant that can yield 1,4-cyclohexanediol as product of NaBH4 reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below;

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

Answer 13

(d)

Interpretation Introduction

Interpretation:The expected reactant that can yield 1,4-cyclohexanediol as product of NaBH4 reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below;

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

Answer 14

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Answer 15

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Answer 16

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Answer 17

Ch. 8.1 - Prob. 8.1E Ch. 8.1 - Prob. 8.2E Ch. 8.3 - Prob. 8.4TIY Ch. 8.3 - Prob. 8.5E Ch. 8.3 - Prob. 8.6E Ch. 8.4 - Prob. 8.7E Ch. 8.5 - Prob. 8.8E Ch. 8.5 - Prob. 8.9E Ch. 8.5 - Prob. 8.10E Ch. 8.5 - Prob. 8.11E

Solution Summary: The author explains that the expected reactant that can yield 1-decanol should be formulated.

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