Concept explainers
Interpretation:
Structural formula for the major product for alkyl bromide, when each of the given alcohols is reacted with hydrogen bromide, is to be drawn using the same format for alkyl bromide as the original given alcohol. IUPAC name for each alkyl bromide including its stereochemistry is to be given.
Concept introduction:
Secondary and tertiary alcohols react with hydrogen halides by the
Primary alcohols and methanol react with hydrogen halides by the
There is a possibility of a formation of a racemic mixture to give a mixture of stereoisomers when optically active alcohols react with hydrogen halides in an
There is an inversion of configuration for the reaction of optically active alcohols with hydrogen halides in an
The three dimensional spatial arrangement of substituents at a chirality center is called the absolute configuration.
The Cahn-Ingold-Prelog rule system ranks the substituents in the chirality center in the order of decreasing
In next step, molecule is oriented such that the bond to the lowest ranked substituent points away from the observer. Then check the path of sequence of decreasing priority. If the path of sequence of decreasing priority is clockwise then the configuration is R and if path of sequence of decreasing priority is anticlockwise, then the confirmation is S.
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Chapter 5 Solutions
Organic Chemistry - Standalone book
- Compound X is known to contain oxygen. The infrared (IR) spectrum of X contains a strong peak around 1100 cm-¹, but there are no absorption bands around 1700 cm-¹ nor in the range of 3100-3600 cm-¹. What class of compound is X? A) aldehyde B) ether C) alcohol D) carboxylic acidarrow_forwardThe synthesis of carbohydrates can be particularly difficult because of the large number of chiral centers and OH functional groups present. Epoxides can be useful synthetic intermediates in carbohydrate synthesis. Draw the product of the reaction of a phenyl Gilman reagent with this epoxide. QAO • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Explicitly define the cis/trans stereochemistry of fused rings using wedge or hash bonds. • If enantiomers are formed, draw both. • Separate multiple products using the sign from the drop-down menu. + e./ 8) 16224 000. Itarrow_forward1) For the following molecule, provide the proper IUPAC name. Be mindful of the stereochemistry. OHarrow_forward
- a. Draw the two chair forms for compound A, being careful to show the stereoisomergiven above. You may use shorthand R in your drawings. Indicate the MAJOR and MINORconformations b. Using curved-arrow convention and the correct chair form of Compound A, show themechanism for the formation of alkene C from Compound A. You may use B: to indicatethe base.arrow_forwardAlkenes can be converted to alcohols by hydroboration-oxidation. (a) Draw the structure of the alcohol or alcohols formed in the reaction sequence. Clearly indicate stereochemistry by drawing a wedged bond, a dashed bond and two in-plane bonds per each chiral carbon. Draw hydrogen atoms that are connected to wedge-and-dash bonds.(b) Characterize the product or products of the reactions. Be sure to draw hydrogens on oxygen, where applicable. Select Draw Rings More Erase H 1. B₂H6, (a) diglyme 2. H2O2, HOT, H₂O ✓ C O Q2 Qarrow_forwardAlkenes can be converted to alcohols by hydroboration-oxidation. (a) Draw the structure of the alcohol or alcohols formed in the reaction sequence. Clearly indicate stereochemistry by drawing a wedged bond, a dashed bond and two in-plane bonds per each chiral carbon. Draw hydrogen atoms that are connected to wedge-and-dash bonds.(b) Characterize the product or products of the reactions. Be sure to draw hydrogens on oxygen, where applicable. H 1. B2H6. diglyme (a) H 2. H2O2, HO-, H20 он OH Incorrectarrow_forward
- Draw the structure of the following three isomeric esters with chemical formula C-H1,0,. Ester #1: (E)-ethyl 2-pentenoate Ester #2: ethyl 3-methyl-3-butenoate Ester #3: (Z)-methyl 3-hexenoate • Consider E/Z stereochemistry of alkenes. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu. opy aste ChemDoodle Previous Next Email Instructor Save and Exitarrow_forwardAlkenes can be converted to alcohols by hydroboration-oxidation. (a) Draw the structure of the alcohol or alcohols formed in the reaction sequence. Clearly indicate stereochemistry by drawing a wedged bond, a dashed bond and two in-plane bonds per each chiral carbon. Draw hydrogen atoms that are connected to wedge-and-dash bonds.(b) Characterize the product or products of the reactions. Be sure to draw hydrogens on oxygen, where applicable. 1. B2H6, diglyme (a) 2. H202, HO¯, H20 OH OH H. Incorrect MacBook Proarrow_forwardAlkenes can be converted to alcohols by hydroboration-oxidation. (a) Draw the structure of the alcohol or alcohols formed in the reaction sequence. Clearly indicate stereochemistry by drawing a wedged bond, a dashed bond and two in-plane bonds per each chiral carbon. Draw hydrogen atoms that are connected to wedge-and-dash bonds.(b) Characterize the product or products of the reactions. Be sure to draw hydrogens on oxygen, where applicable. Select Draw Rings More Erase C 1. B2H6, diglyme (a) 2. H2O2, HO¯, H2Oarrow_forward
- Alkenes can be converted to alcohols by hydroboration-oxidation. (a) Draw the structure of the alcohol or alcohols formed in the reaction sequence. Clearly indicate stereochemistry by drawing a wedged bond, a dashed bond and two in-plane bonds per each chiral carbon. Draw hydrogen atoms that are connected to wedge-and-dash bonds.(b) Characterize the product or products of the reactions. Be sure to draw hydrogens on oxygen, where applicable. Select Draw Rings More Erase H 1. B,H§, diglyme (a) 2. H2O2, HO", H2Oarrow_forwardDraw the structural formula of the major product of the reaction of (S)-2,2,3-trimethyloxirane with Me,NH. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Include H atoms at chiral centers only. • If a group is achiral, do not use wedged or hashed bonds on it.arrow_forward1. Provide appropriate IUPAC names for the following molecules. Do not forget to include the stereochemical information necessary to completely describe the compound. LI -Itt.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning