Concept explainers
a) Bromoacetone
Interpretation:
The structure for bromoacetone is to be shown.
Concept introduction:
To show:
The structure for bromoacetone.
Answer to Problem 54AP
The structure of bromoacetone is
Explanation of Solution
The name indicates that the compound is a ketone with three carbon straight chain with a bromine atom attached to C1.
The structure of bromoacetone is
b) (S)-2-Hydroxypropanal
Interpretation:
The structure for (S)-2-hydroxypropanal is to be shown.
Concept introduction:
To show:
The structure for (S)-2-hydroxypropanal.
Answer to Problem 54AP
The structure of (S)-2-hydroxypropanal is
Explanation of Solution
The name indicates that the compound is an aldehyde with three carbon straight chain with a hydroxyl group attached to C2. The molecule is chiral. The three groups, -OH(first highest priority), -CHO (second highest priority) and -CH3(third highest priority) are arranged anticlockwise when viewed from the side away from H (fourth highest priority). Hence it has S stereochemistry.
The structure of (S)-2-hydroxypropanal is
c) 2-Methyl-3-heptanone
Interpretation:
The structure for 2-methyl-3-heptanone is to be shown.
Concept introduction:
Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.
To show:
The structure for 2-methyl-3-heptanone.
Answer to Problem 54AP
The structure of 2-methyl-3-heptanone is
Explanation of Solution
The name indicates that the compound is a ketone with seven carbon straight chain having the keto group at position three and a methyl group attached to C2.
The structure of 2-methyl-3-heptanone is
d) (2S,3R)-2,3,4-Trihydroxybutanal
Interpretation:
The structure for (2S,3R)-2,3,4-trihydroxybutanal is to be shown.
Concept introduction:
Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.
To show:
The structure for (2S,3R)-2,3,4-trihydroxybutanal.
Answer to Problem 54AP
The structure of (2S,3R)-2,3,4-trihydroxybutanal is
Explanation of Solution
The name indicates that the compound is an aldehyde with four carbon straight chain and has three hydroxyl groups attached to C2, C3 and C4.
The molecule is chiral. The C2 is attached to the three groups, -OH(first highest priority), -CHO (second highest priority) and –C3 (third highest priority) arranged anticlockwise when viewed from the side away from H (fourth highest priority). Hence it has S stereochemistry.
The C3 is attached to the three groups, -OH(first highest priority), –C2 (second highest priority) and –CH2OH--(third highest priority) arranged clockwise when viewed from the side away from H (fourth highest priority). Hence it has R stereochemistry.
The structure of (2S,3R)-2,3,4-trihydroxybutanal is
e) 2,2,4,4-Tetramethyl-3-pentanone
Interpretation:
The structure for 2,2,4,4-tetramethyl-3-pentanone is to be shown.
Concept introduction:
Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.
To show:
The structure for 2,2,4,4-tetramethyl-3-pentanone.
Answer to Problem 54AP
The structure of 2,2,4,4-tetramethyl-3-pentanone is
Explanation of Solution
The name indicates that the compound is a ketone with five carbon straight chain with a keto group at position three attached to four methyl groups, two on C2 and other two on C4.
The structure of 2,2,4,4-Tetramethyl-3-pentanone is
f) 4-methyl-3-penten-2-one
Interpretation:
The structure for 4-methyl-3-penten-2-one is to be shown.
Concept introduction:
Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.
To show:
The structure for 4-methyl-3-penten-2-one.
Answer to Problem 54AP
The structure of 4-methyl-3-penten-2-one is
Explanation of Solution
The name indicates that the compound is a ketone containing a five carbon straight chain, having a keto group at position two and a double bond between C3 and C4 with a methyl group on C4.
The structure of 4-methyl-3-penten-2-one is
g) Butanedial
Interpretation:
The structure for butanedial is to be shown.
Concept introduction:
Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.
To show:
The structure for butanedial.
Answer to Problem 54AP
The structure of butanedial is
Explanation of Solution
The name of the compound indicates that it has a four carbon straight chain with two aldehyde groups at both ends.
The structure of butanedial is
h) 3-Phenyl-2-propenal
Interpretation:
The structure for 3-phenyl-2-propenal is to be shown.
Concept introduction:
Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.
To show:
The structure for 3-phenyl-2-propenal.
Answer to Problem 54AP
The structure of 3-phenyl-2-propenal is
Explanation of Solution
The name of the compound indicates that the compound is a three carbon aldehyde with a double bond between C2 & C3 and has a phenyl group attached to C3.
The structure of 3-phenyl-2-propenal is
i) 6,6-Dimethyl-2,4-cyclohexadienone
Interpretation:
The structure for 6,6-dimethyl-2,4-cyclohexadienone is to be shown.
Concept introduction:
Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.
To show:
The structure for 6,6-dimethyl-2,4-cyclohexadienone.
Answer to Problem 54AP
The structure of 6,6-dimethyl-2,4-cyclohexadienone is
Explanation of Solution
The name of the compound indicates that it is a cyclic ketone with a cyclohexadiene ring containing two double bonds, one between C2 & C3 and other between C4 & C5. It also has two methyl groups on C6.
The structure of 6,6-dimethyl-2,4-cyclohexadienone is
j) p-Nitroacetophenone
Interpretation:
The structure for p-nitroacetophenone is to be shown.
Concept introduction:
Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo. Some common names like acetophenone are retained by IUPAC.
To show:
The structure for p-nitroacetophenone.
Answer to Problem 54AP
The structure of p-nitroacetophenone is
Explanation of Solution
The name of the compound indicates that it contains an actyl and nitro groups attached to a benzene ring in para relationship.
The structure of p-nitroacetophenone is
Want to see more full solutions like this?
Chapter 19 Solutions
Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th
- Denote the dipole for the indicated bonds in the following molecules. ✓ H3C CH3 B F-CCl3 Br-Cl H3C —Si(CH3)3 CH3 OH HO HO H HO OH vitamin Carrow_forward(a) What is the hybridization of the carbon in the methyl cation (CH3*) and in the methyl anion (CH3)? (b) What is the approximate H-C-H bond angle in the methyl cation and in the methyl anion?arrow_forward10:16 ☑ Vo)) Vo) 4G LTE 76% Complete the following reaction by identifying the principle organic product of the reaction. HO OH ↑ CH2N2 OH ? ○ A. 01 N₂H2C OH ОН B. HO OCH3 OH ○ C. HO OH ŎCH₂N2 ○ D. H3CO OH он Quiz navigation 1 2 3 4 5 11 12 Next page 10 6 7 8 9 10arrow_forward
- Which one of the following statements explain why protecting groups are referred to as “a necessary evil in organic synthesis”? Question 12Select one or more: A. They increase the length and cost of the synthesis B. Every synthesis employs protecting groups C. Protecting group have no role to play in a synthesis D. They minimize the formation of side productsarrow_forwardWhich of the following attributes is a key advantage of the chiral auxiliary approach over the chiral pool approach in asymmetric synthesis? Question 10Select one: A. Chiral auxiliaries are cheaper than chiral pool substrates B. Chiral auxiliary can be recovered and recycled unlike chiral pool substrates. C. The use of chiral auxiliaries provide enantiopure products, while chiral pool reactions are only enantioselective D. The chiral auxiliaries are naturally occurring and do not require synthesisarrow_forwardIn the following molecule, indicate the hybridization and shape of the indicated atoms. CH3 CH3 H3C HO: CI:arrow_forward
- Which of the following are TRUE about linear syntheses? Question 7Select one: A. They are easier to execute B. They are the most efficient strategy for all syntheses C. They are generally shorter than convergent syntheses D. They are less versatile compared to convergent synthesesarrow_forwardWhich of the following characteristics is common among chiral pool substrates? Question 4Select one: A. They have good leaving groups B. They are all achiral C. All have a multiplicity of chiral centres D. They have poor leaving groupsarrow_forwardDetermine whether the following reaction is an example of a nucleophilic substitution reaction: H NO2 H+ NO 2 + Molecule A Molecule B Is this a nucleophilic substitution reaction? If this is a nucleophilic substitution reaction, answer the remaining questions in this table. What word or two-word phrase is used to describe the role Molecule A plays in this reaction? What word or two-word phrase is used to describe the role Molecule B plays in this reaction? Use a 6 + symbol to label the electrophilic carbon that is attacked during the substitution. Highlight the leaving group on the appropriate reactant. O Yes ○ No ☐ 0 dx 000 HE ?arrow_forward
- Draw the major organic product of the Bronsted acid-base reaction. Include all lone pairs and charges as appropriate. Ignore any counterions. :0: NaOH Harrow_forward5. Calculate the total amount of heat transferred as 50 g of wat Specific heat H₂O (g) 2.00 J/g°C -10 °C. Specific heat H₂O (1) Specific heat H₂O (s) 4.18 J/g°C 2.11 J/g°C Heat of vaporization 2260 J/g Heat of fusion 334 J/g Melting point 0°C 6. Calculate the total amount of heat transferred as 25 g of water is heated from 50 °C to 100 °C as a gas. Boiling point 100 °Carrow_forwardCalculate the total amount of heat transferred as 50 g of Water -10°C. Calculate the total amount of heat transferred as 25 g of water is heated from 50°C to 100°C as a gas. \table[[Specific heat H₂O(g), 2.00°C Η 2 g 5. Calculate the total amount of heat transferred as 50 g of wat Specific heat H₂O (g) 2.00 J/g°C -10 °C. 4.18 J/g°C 2.11 J/g°C 2260 J/g 334 J/g Specific heat H₂O (1) Specific heat H₂O (s) Heat of vaporization Heat of fusion Melting point 6. Calculate the total amount of heat transferred as 25 g of water is heated from 50 °C to 100 °C as a gas. Boiling point 100 °C 0°Carrow_forward
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning